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ELECTRONIC SUPPORTING INFORMATION Ermal Ismalaj a, Giacomo Strappaveccia a, Eleonora Ballerini a, Fausto Elisei a, Oriana Piermatti a, Dmitri Gelman b, Luigi Vaccaro a a CEMIN - Dipartimento di Chi mica, Biologia e Biot ecnologie, Università di Perugia Via Elce di Sotto, 8; Perugia, Italia. Fax: +39 075 5855560; Tel: +39 075 5855541; E-mail: luigi.vaccaro@unipg.it. b Institute of Chemistry, The Hebrew University, Edm ond Safra Campus, Givat Ra m, 91904 Jerusalem (Israel). CONTENTS page ESI1 - ESI 2 Experimental Section pages ESI 3 ESI 22 Full characterization data ( 1 H NMR, 13 C NMR, EA, GC-EIMS) for Compounds 3a-m pages ESI 23 - ESI 48 Copies of the 1 H and 13 C NMR for compounds 3a-m SI - 1

Experimental Section Unless otherwise stated, all solvents and reagents were used as obtained from commercial sources without further purification. GLC analyses were performed by using Hewlett-Packard HP 5890A equipped with a capillary column DB-35MS (30 m, 0.53 mm), a FID detector and hydrogen as gas carrier. GC-EIMS analyses were carried out by using a Hewlett-Packard HP 6890N Network GC system/5975 Mass Selective Detector equipped with an electron impact ionizer at 70 ev. NMR spectra were recorded on a Bruker DRX-ADVANCE 400 MHz ( 1 H at 400 MHz and 13 C at 100.6 MHz) in CDCl 3 using TMS as the internal standard. Elemental Analyses were conducted on a Fisons EA1108CHN. Melting points are not corrected and they were measured on a Büchi 510. Compounds 3a, 1 3b, 2 3c, 1 3d, 2 3e, 1 3f, 3 3g, 1 3h, 4 3i, 5 3j, 5 3k, 6 3l, 1 3m 7 are known compounds. Characterization data and copies of the 1 H and 13 C NMR are reported below. Reference: 1. T. Yanase, Y. Monguchi, H. Sajiki, RSC Adv., 2012, 2, 590 594. 2. C. Premi, N. Jain, Eur. J. Org. Chem., 2013, 5493 5499. 3. Y. Monguchi, T. Yanase, S. Mori, H. Sajiki, Synthesis, 2013, 40-44. 4. T. Yanase, S. Mori, Y. Monguchi, H. Sajiki, Chem. Lett., 2011, 40, 910-912. 5. B. Inés, R. SanMartin, F. Churruca, E. Domínguez, M. K. Urtiaga, M. I. Arriortua, Organometallics, 2008, 27, 2833 2839. 6. V. K. R. Kumar, S. Krishnakumar, K. R. Gopidas, Eur. J. Org. Chem., 2012, 3447-3458. 7. T. M. Razler, Y. Hsiao, F. Qian, R. Fu, R. K. Khan, W. Doubleday, J. Org. Chem., 2009, 74, 1381-1384. SI - 2

Chem. Name 4-nitro-1,1'-biphenyl (3a) Lit. Ref. RSC Adv., 2012, 2, 590 594 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromo-4-nitrobenzene (1a) (204 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3a was obtained as a solid (165 mg, 83% yield). Mol Formula C 12 H 9 NO 2 m.p. 116-118 C Elemental Analysis: Calc.: C, 72.35; H, 4.55; N, 7.03. Found: C, 72.40; H, 4.65; N, 7.00 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 7.43-7.54 3 m 7.62-7.64 2 m 7.74 2 d 8.8 8.30 2 d 8.8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 124.2, 127.5, 127.9, 129.0, 129.3, 138.9, 147.2, 147.8 GC-EIMS (m/z, %): 200 (10), 199 (M +, 83), 169 (44), 153 (31), 152 (100), 151 (33), 150 (11), 141 (40), 127 (11), 126 (11), 115 (19), 77 (12), 76 (14), 63 (13), 51 (12), 50 (10) SI - 3

Chem. Name 4-nitro-1,1'-biphenyl (3a) Lit. Ref. RSC Adv., 2012, 2, 590 594 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-iodo-4-nitrobenzene (4a) (254 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3a was obtained as a solid (155 mg, 78% yield). Mol Formula C 12 H 9 NO 2 m.p. 116-118 C Elemental Analysis: Calc.: C, 72.35; H, 4.55; N, 7.03. Found: C, 72.42; H, 4.67; N, 7.05 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 7.43-7.54 3 m 7.62-7.64 2 m 7.74 2 d 8.8 8.30 2 d 8.8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 124.2, 127.5, 127.9, 129.0, 129.3, 138.9, 147.2, 147.8 GC-EIMS (m/z, %): 200 (10), 199 (M +, 83), 169 (44), 153 (31), 152 (100), 151 (33), 150 (11), 141 (40), 127 (11), 126 (11), 115 (19), 77 (12), 76 (14), 63 (13), 51 (12), 50 (10) SI - 4

Chem. Name 1,1'-biphenyl (3b) Lit. Ref. Eur. J. Org. Chem. 2013, 5493 5499 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), bromobenzene (1b) (158 mg, 0.107 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3b was obtained as a solid (145 mg, 94% yield). Mol Formula C 12 H 10 m.p. 68-70 C Elemental Analysis: Calc.: C, 93.46; H, 6.54. Found: C, 93.50; H, 6.60 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 7.35-7.39 2 m 7.45-7.48 4 m 7.61-7.63 4 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 127.3, 127.4, 128.9, 141.4 GC-EIMS (m/z, %): 155 (13), 154 (M +, 100), 153 (40), 152 (29), 76 (11) SI - 5

Chem. Name 1,1'-biphenyl (3b) Lit. Ref. Eur. J. Org. Chem., 2013, 5493 5499 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), iodobenzene (4b) (208 mg, 0.114 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3b was obtained as a solid (142 mg, 92% yield). Mol Formula C 12 H 10 m.p. 68-70 C Elemental Analysis: Calc.: C, 93.46; H, 6.54. Found: C, 93.51; H, 6.64 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 7.35-7.39 2 m 7.45-7.48 4 m 7.61-7.63 4 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 127.3, 127.4, 128.9, 141.4 GC-EIMS (m/z, %): 155 (13), 154 (M +, 100), 153 (40), 152 (29), 76 (11) SI - 6

Chem. Name 4-methyl-1,1'-biphenyl (3c) Lit. Ref. RSC Adv., 2012, 2, 590 594 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromo-4-methylbenzene (1c) (174 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3c was obtained as a solid (145 mg, 86% yield). Mol Formula C 13 H 12 m.p. 45-47 C Elemental Analysis: Calc.: C, 92.81; H, 7.19. Found: C, 92.75; H, 7.27 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.41 3 s 7.26-7.28 2 m 7.32-7.36 1 m 7.42-7.46 2 m 7.50-7.52 2 m 7.59-7.61 2 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 21.2, 127.09, 127.11, 128.8, 129.6, 137.1, 138.4, 141.3 GC-EIMS (m/z, %): 169 (14), 168 (M +, 100), 167 (66), 165 (28), 153 (15), 152 (21), 115 (11) SI - 7

Chem. Name 4-methyl-1,1'-biphenyl (3c) Lit. Ref. RSC Adv., 2012, 2, 590 594 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-iodo-4-methylbenzene (4c) (220 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3c was obtained as a solid (135 mg, 80% yield). Mol Formula C 13 H 12 m.p. 45-47 C Elemental Analysis: Calc.: C, 92.81; H, 7.19. Found: C, 92.74; H, 7.28 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.41 3 s 7.26-7.28 2 m 7.32-7.36 1 m 7.42-7.46 2 m 7.50-7.52 2 m 7.59-7.61 2 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 21.2, 127.09, 127.11, 128.8, 129.6, 137.1, 138.4, 141.3 GC-EIMS (m/z, %): 169 (14), 168 (M +, 100), 167 (66), 165 (28), 153 (15), 152 (21), 115 (11) SI - 8

Chem. Name 1-phenylnaphthalene (3d) Lit. Ref. Eur. J. Org. Chem., 2013, 5493 5499 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromonaphthalene (1d) (213 mg, 0.144 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3d was obtained as a solid (167 mg, 82% yield). Mol Formula C 16 H 12 m.p. 44-46 C Elemental Analysis: Calc.: C, 94.08; H, 5.92. Found: C, 94.15; H, 5.85 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 7.47-7.61 9 m 7.92-8.00 3 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 125.5, 125.9, 126.13, 126.14, 127.0, 127.3, 127.7, 128.37, 128.38, 130.2, 131.7, 133.9, 140.4, 140.9 GC-EIMS (m/z, %): 204 (M +, 100), 203 (98), 202 (61), 201 (13), 200 (13), 101 (16) SI - 9

Chem. Name 1-([1,1'-biphenyl]-4-yl)ethanone (3e) Lit. Ref. RSC Adv., 2012, 2, 590 594 Br O 1e + Si(OEt) 3 TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h 1.5 eq. 2a 3e O Molecular Weight: 196 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-(4-bromophenyl)ethanone (1e) (203 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3e was obtained as a solid (153 mg, 78% yield). Mol Formula C 14 H 12 O m.p. 115-118 C Elemental Analysis: Calc.: C, 85.68; H, 6.16. Found: C, 85.78; H, 6.10 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.64 3 s 7.38-7.42 1 m 7.46-7.49 2 m 7.62-7.64 2 m 7.69 2 d 8.4 8.04 2 d 8.4 13 C NMR (100.6 MHz, CDCl 3 ) δ : 26.8, 127.3, 127.4, 128.4, 129.0, 129.1, 136.0, 140.0, 145.9, 197.9 GC-EIMS (m/z, %): 196 (M +, 48), 182 (14), 181 (100), 153 (42), 152 (69), 151 (21), 76 (11), 43 (12) SI - 10

Chem. Name 1-([1,1'-biphenyl]-3-yl)ethanone (3f) Lit. Ref. Synthesis, 2013, 40-44 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-(3-bromophenyl)ethanone (1f) (204 mg, 0.136 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3f was obtained as a solid (145 mg, 74% yield). Mol Formula C 14 H 12 O m.p. 38-41 C Elemental Analysis: Calc.: C, 85.68; H, 6.16. Found: C, 85.80; H, 6.12 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.66 3 s 7.37-7.41 1 m 7.46-7.49 2 m 7.52-7.56 1 m 7.62-7.64 2 m 7.80 1 d 7.6 7.94 1 d 7.6 8.19 1 s 13 C NMR (100.6 MHz, CDCl 3 ) δ : 26.9, 127.1, 127.31, 127.32, 127.9, 129.0, 129.2, 131.9, 137.8, 140.3, 141.9, 198.2 GC-EIMS (m/z, %): 196 (M +, 66), 182 (14), 181 (100), 153 (68), 152 (82), 151 (25), 76 (13), 43 (19) SI - 11

Chem. Name 4-methoxy-1,1'-biphenyl (3g) Lit. Ref. RSC Adv., 2012, 2, 590 594 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromo-4-methoxybenzene (1g) (188 mg, 0.126 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 0.369 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3g was obtained as a solid (144 mg, 78% yield). Mol Formula C 13 H 12 O m.p. 87-89 C Elemental Analysis: Calc.: C, 84.75; H, 6.57. Found: C, 84.87; H, 6.55 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.86 3 s 6.99 2 d 8.8 7.29-7.32 1 m 7.40-7.44 2 m 7.52-7.57 4 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.3, 126.8, 126.9, 128.3, 128.8, 133.9, 141.0, 159.3 GC-EIMS (m/z, %): 185 (14), 184 (M +, 100), 169 (51), 141 (61), 139 (17), 115 (53) SI - 12

Chem. Name 4-methoxy-1,1'-biphenyl (3g) Lit. Ref. RSC Adv., 2012, 2, 590 594 Br Si(OEt) 3 1b + O 1.5 eq. 2b TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h 3g O Molecular Weight: 184 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), bromobenzene (1b) (158 mg, 0.107 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3g was obtained as a solid (149 mg, 81% yield). Mol Formula C 13 H 12 O m.p. 87-89 C Elemental Analysis: Calc.: C, 84.75; H, 6.57. Found: C, 84.88; H, 6.53 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.86 3 s 6.99 2 d 8.8 7.29-7.32 1 m 7.40-7.44 2 m 7.52-7.57 4 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.3, 126.8, 126.9, 128.3, 128.8, 133.9, 141.0, 159.3 GC-EIMS (m/z, %): 185 (14), 184 (M +, 100), 169 (51), 141 (61), 139 (17), 115 (53) SI - 13

Chem. Name 4-methoxy-1,1'-biphenyl (3g) Lit. Ref. RSC Adv., 2012, 2, 590 594 I Si(OEt) 3 4b + O 1.5 eq. 2b TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h 3g O Molecular Weight: 184 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), iodobenzene (4b) (208 mg, 0.114 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3g was obtained as a solid (148 mg, 80% yield). Mol Formula C 13 H 12 O m.p. 87-89 C Elemental Analysis: Calc.: C, 84.75; H, 6.57. Found: C, 84.86; H, 6.60 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.86 3 s 6.99 2 d 8.8 7.29-7.32 1 m 7.40-7.44 2 m 7.52-7.57 4 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.3, 126.8, 126.9, 128.3, 128.8, 133.9, 141.0, 159.3 GC-EIMS (m/z, %): 185 (14), 184 (M +, 100), 169 (51), 141 (61), 139 (17), 115 (53) SI - 14

Chem. Name 4-methoxy-4'-methyl-1,1'-biphenyl (3h) Lit. Ref. Chem. Lett., 2011, 40, 910-912 Br Si(OEt) 3 1c + O 1.5 eq. 2b TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h O 3h Molecular Weight: 198 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromo-4-methylbenzene (1c) (174 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3h was obtained as a solid (161 mg, 81% yield). Mol Formula C 14 H 14 O m.p. 110-112 C Elemental Analysis: Calc.: C, 84.81; H, 7.12. Found: C, 84.75; H, 7.08 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.41 3 s 3.87 3 s 6.99 2 d 8 7.25 2 d 8 7.47 2 d 8 7.53 2 d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 21.0, 55.2, 114.1, 126.5, 127.9, 129.4, 133.7, 136.3, 137.9, 158.8 GC-EIMS (m/z, %): 199 (14), 198 (M +, 100), 183 (59), 155 (44), 154 (11), 153 (17), 152 (17), 128 (16), 127 (10), 115 (12) SI - 15

Chem. Name 4-methoxy-4'-methyl-1,1'-biphenyl (3h) Lit. Ref. Chem. Lett., 2011, 40, 910-912 I Si(OEt) 3 4c + O 1.5 eq. 2b TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h O 3h Molecular Weight: 198 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-iodo-4-methylbenzene (4c) (220 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3h was obtained as a solid (158 mg, 80% yield). Mol Formula C 14 H 14 O m.p. 110-112 C Elemental Analysis: Calc.: C, 84.81; H, 7.12. Found: C, 84.77; H, 7.11 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.41 3 s 3.87 3 s 6.99 2 d 8 7.25 2 d 8 7.47 2 d 8 7.53 2 d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 21.0, 55.2, 114.1, 126.5, 127.9, 129.4, 133.7, 136.3, 137.9, 158.8 GC-EIMS (m/z, %): 199 (14), 198 (M +, 100), 183 (59), 155 (44), 154 (11), 153 (17), 152 (17), 128 (16), 127 (10), 115 (12) SI - 16

Chem. Name 4,4'-dimethoxy-1,1'-biphenyl (3i) Lit. Ref. Organometallics, 2008, 27, 2833 2839 Br Si(OEt) 3 + TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h O O O 1g O 1.5 eq. 2b 3i Molecular Weight: 214 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromo-4-methoxybenzene (1g) (188 mg, 0.126 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3i was obtained as a solid (195 mg, 91% yield). Mol Formula C 14 H 14 O 2 m.p. 177-180 C Elemental Analysis: C, 78.48; H, 6.59. Found: C, 78.44; H, 6.64 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.85 6 s 6.96 4 d 8 7.48 4 d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.3, 127.9, 133.6, 158.8 GC-EIMS (m/z, %): 215 (16), 214 (M +, 100), 200 (14), 199 (95), 171 (45), 156 (17), 139 (14), 128 (34), 127 (11), 102 (10) SI - 17

Chem. Name 4-methoxy-4'-nitro-1,1'-biphenyl (3j) Lit. Ref. Organometallics, 2008, 27, 2833 2839 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromo-4-nitrobenzene (1a) (204 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3j was obtained as a solid (186 mg, 81% yield). Mol Formula C 13 H 11 NO 3 m.p. 107-110 C Elemental Analysis: Calc.: C, 68.11; H, 4.84; N, 6.11. Found: C, 68.21; H, 4.90; N, 6.05 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.88 3 s 7.02 2 d 8 7.58 2 d 8 7.69 2 d 8 8.27 2 d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.7, 124.2, 127.1, 128.7, 131.1, 146.6, 147.3, 160.5 GC-EIMS (m/z, %): 230 (14), 229 (M +, 100), 199 (25), 183 (11), 171 (18), 168 (24), 152 (18), 140 (31), 139 (57), 128 (13) SI - 18

Chem. Name 4-methoxy-4'-nitro-1,1'-biphenyl (3j) Lit. Ref. Organometallics, 2008, 27, 2833 2839 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-iodo-4-nitrobenzene (4a) (254 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3j was obtained as a solid (179 mg, 78% yield). Mol Formula C 13 H 11 NO 3 m.p. 107-110 C Elemental Analysis: Calc.: C, 68.11; H, 4.84; N, 6.11. Found: C, 68.19; H, 4.80; N, 6.04 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.88 3 s 7.02 2 d 8 7.58 2 d 8 7.69 2 d 8 8.27 2 d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.7, 124.2, 127.1, 128.7, 131.1, 146.6, 147.3, 160.5 GC-EIMS (m/z, %): 230 (14), 229 (M +, 100), 199 (25), 183 (11), 171 (18), 168 (24), 152 (18), 140 (31), 139 (57), 128 (13) SI - 19

Chem. Name 1-(4-methoxyphenyl)naphthalene (3k) Lit. Ref. Eur. J. Org. Chem., 2012, 3447-3458 Br Si(OEt) 3 1d + O 1.5 eq. 2b TBAF (1.5 eq.), Pd/C (0.5 mol%) GVL (1M), 130 C, 24 h O 3k Molecular Weight: 234 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-bromonaphthalene (1d) (213 mg, 0.144 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether). 3k was obtained as a solid (185 mg, 79% yield). Mol Formula C 17 H 14 O m.p. 114-116 C Elemental Analysis: Calc.: C, 87.15; H, 6.02. Found: C, 87.45; H, 6.05 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 3.90 3 s 7.04 2 d 8.4 7.40-7.53 6 m 7.83-7.85 1 m 7.89 2 m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 113.8, 125.5, 125.8, 126.0, 126.2, 127.0, 127.4, 128.5, 131.2, 132.0, 133.2, 134.0, 140.0, 159.1 GC-EIMS (m/z, %): 235 (31), 234 (M +, 100), 219 (50), 203 (15), 202 (11), 191 (33), 190 (39), 189 (56), 101 (10), 94 (11) SI - 20

Chem. Name 1-(4'-methoxy-[1,1'-biphenyl]-4-yl)ethanone (3l) Lit. Ref. RSC Adv., 2012, 2, 590 594 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-(4-bromophenyl)ethanone (1e) (204 mg, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3l was obtained as a solid (170 mg, 75% yield). Mol Formula C 15 H 14 O 2 m.p. 153-156 C Elemental Analysis: Calc.: C, 79.62; H, 6.24. Found: C, 79.71; H, 6.17 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.63 3 s 3.86 3 s 7.00 2 d 8 7.58 2 d 8 7.65 2 d 8 8.01 2 d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 26.8, 55.5, 114.5, 126.7, 128.5, 129.1, 132.4, 135.4, 145.5, 160.0, 197.9 GC-EIMS (m/z, %): 227 (10), 226 (M +, 55), 212 (12), 211 (100), 183 (13), 168 (20), 152 (12), 140 (29), 139 (49), 63 (11), 43 (18) SI - 21

Chem. Name 1-(4'-methoxy-[1,1'-biphenyl]-3-yl)ethanone (3m) Lit. Ref. J. Org. Chem., 2009, 74, 1381-1384 METHOD: In a screw capped vial equipped with a magnetic stirrer Pd/C 10% wt. (5.3 mg, 0.5 mmol%), GVL (1 ml), TBAF (488 mg, 1.5 mmol), 1-(3-bromophenyl)ethanone (1f) (204 mg, 0.136 ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 0.406 ml, 1.5 mmol) was added and the mixture was heated at 130 C under an atmosphere of argon. After 24 h water was added, the formed precipitate was filtered off, washed with water and purified by column chromatography (petroleum ether : EtOAc / 95 : 5). 3m was obtained as a solid (181 mg, 80% yield). Mol Formula C 15 H 14 O 2 m.p. 55-57 C Elemental Analysis: Calc.: C, 79.62; H, 6.24. Found: C, 79.69; H, 6.19 1 H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz 2.65 3 s 3.85 3 s 6.99 2 d 8 7.48-7.52 1 m 7.54-7.57 2 m 7.74 1 d 8 7.88 1 d 8 8.14 1 s 13 C NMR (100.6 MHz, CDCl 3 ) δ : 26.8, 55.4, 114.4, 126.5, 126.7, 128.3, 129.1, 131.3, 132.6, 137.6, 141.3, 159.6, 198.3 GC-EIMS (m/z, %): 227 (16), 226 (M +, 100), 212 (11), 211 (88), 183 (44), 168 (35), 153 (11), 152 (28), 140 (39), 139 (76), 63 (10) SI - 22

8.316 8.294 7.753 7.732 7.639 7.621 7.523 7.505 7.486 7.468 7.450 7.432 7.260 4 nitro 1,1 biphenyl (3a) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 2.000 2.085 2.080 3.145 SI - 23

147.752 147.176 138.881 129.284 129.047 127.929 127.514 124.240 77.472 77.155 76.837 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 24

7.629 7.610 7.484 7.465 7.446 7.388 7.369 7.351 7.261 1,1 biphenyl (3b) 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 4.000 4.067 2.130 SI - 25

141.350 128.882 127.379 127.297 77.469 77.149 76.832 1,1 biphenyl (3b) 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 26

141.260 138.455 137.142 129.600 128.833 127.112 127.092 77.467 77.148 76.832 21.232 4 methyl 1,1 biphenyl ( ) 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 27

141.260 138.455 137.142 129.600 128.833 127.112 127.092 77.467 77.148 76.832 21.232 4 methyl 1,1 biphenyl ( ) 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 28

8.001 7.981 7.962 7.936 7.915 7.607 7.589 7.571 7.555 7.535 7.525 7.509 7.492 7.476 7.472 7.260 1 phenylnaphthalene ( ) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 3.000 8.756 SI - 29

140.884 140.380 133.922 131.748 130.188 128.381 128.367 127.745 127.341 127.039 126.144 126.130 125.873 125.489 77.467 77.150 76.832 1 phenylnaphthalene ( ) 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 30

8.047 8.026 7.700 7.679 7.641 7.622 7.494 7.476 7.456 7.422 7.404 7.385 7.259 2.641 1 ([1,1 biphenyl] 4 yl)ethanone (3e) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 2.000 2.023 2.059 2.043 1.026 3.033 SI - 31

197.867 145.908 140.003 135.987 129.078 129.036 128.355 127.395 127.347 77.468 77.150 76.831 26.781 1 ([1,1 biphenyl] 4 yl)ethanone (3e) 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 32

8.189 7.949 7.930 7.806 7.787 7.635 7.616 7.563 7.543 7.524 7.494 7.475 7.456 7.410 7.392 7.374 7.260 2.663 1 ([1,1 biphenyl] 3 yl)ethanone ( ) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 0.997 1.000 1.032 2.056 1.059 2.033 1.004 3.079 SI - 33

198.202 141.863 140.320 137.778 131.867 129.169 129.052 127.939 127.325 127.310 127.091 77.468 77.152 76.834 26.882 1 ([1,1 biphenyl] 3 yl)ethanone ( ) 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 34

7.567 7.547 7.525 7.439 7.420 7.401 7.325 7.306 7.288 7.260 6.997 6.975 3.858 4 methoxy 1,1 biphenyl (3g) 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 4.047 2.025 0.993 2.000 3.077 SI - 35

159.281 140.969 133.924 128.848 128.288 126.873 126.786 114.335 77.463 77.147 76.829 55.483 4 methoxy 1,1 biphenyl (3g) 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 36

7.546 7.525 7.485 7.465 7.260 7.240 7.001 6.980 3.867 2.409 4 methoxy 4 methyl 1,1 biphenyl ( ) 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 1.948 2.009 2.087 2.000 3.123 3.070 SI - 37

158.853 137.892 136.264 133.671 129.354 127.869 126.501 114.080 77.259 76.941 76.623 55.254 20.968 4 methoxy 4 methyl 1,1 biphenyl ( ) 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 38

7.491 7.470 7.263 6.973 6.951 3.848 4,4 dimethoxy 1,1 biphenyl ( ) 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 4.000 4.011 6.152 SI - 39

158.832 133.629 127.870 114.299 77.463 77.147 76.829 55.484 4,4 dimethoxy 1,1 biphenyl ( ) 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 40

8.283 8.262 7.705 7.684 7.595 7.574 7.260 7.033 7.011 3.877 4 methoxy 4 nitro 1,1 biphenyl ( ) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 1.882 1.961 2.016 2.014 3.000 SI - 41

160.543 147.284 146.607 131.123 128.655 127.142 124.227 114.698 77.463 77.145 76.828 55.514 4 methoxy 4 nitro 1,1 biphenyl ( ) 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 42

7.938 7.915 7.893 7.852 7.832 7.533 7.514 7.494 7.471 7.442 7.420 7.402 7.260 7.050 7.029 3.902 1 (4 methoxyphenyl)naphthalene ( ) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 0.5 ppm 2.040 1.041 6.159 2.000 3.016 SI - 43

159.061 140.027 133.962 133.238 131.950 131.233 128.379 127.451 127.030 126.188 126.040 125.820 125.527 113.834 77.467 77.150 76.832 55.463 1 (4 methoxyphenyl)naphthalene ( ) 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 44

8.019 7.998 7.656 7.635 7.592 7.571 7.260 7.013 6.991 3.864 2.630 1 (4 methoxy [1,1 biphenyl] 4 yl)ethanone ( ) 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 0.5 ppm 2.003 2.014 2.028 2.015 3.018 3.000 SI - 45

197.916 160.013 145.488 135.367 132.350 129.078 128.498 126.738 114.512 77.466 77.149 76.830 55.513 26.786 1 (4 methoxy [1,1 biphenyl] 4 yl)ethanone ( ) 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 46

8.144 7.890 7.870 7.752 7.732 7.565 7.544 7.518 7.499 7.480 7.260 7.006 6.984 3.849 2.645 1 (4 methoxy [1,1 biphenyl] 3 yl)ethanone ( ) 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 0.998 1.002 1.034 2.067 1.085 2.084 3.204 3.199 SI - 47

198.294 159.574 141.312 137.610 132.641 131.349 129.056 128.278 126.682 126.467 114.394 77.466 77.148 76.831 55.406 26.837 1 (4 methoxy [1,1 biphenyl] 3 yl)ethanone ( ) 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm SI - 48