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- Ευτέρπη Αλεβιζόπουλος
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1 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: ; Tel: ; luigi.vaccaro@unipg.it. b Institute of Chemistry, The Hebrew University, Edm ond Safra Campus, Givat Ra m, 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
2 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 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, C. Premi, N. Jain, Eur. J. Org. Chem., 2013, Y. Monguchi, T. Yanase, S. Mori, H. Sajiki, Synthesis, 2013, T. Yanase, S. Mori, Y. Monguchi, H. Sajiki, Chem. Lett., 2011, 40, B. Inés, R. SanMartin, F. Churruca, E. Domínguez, M. K. Urtiaga, M. I. Arriortua, Organometallics, 2008, 27, V. K. R. Kumar, S. Krishnakumar, K. R. Gopidas, Eur. J. Org. Chem., 2012, T. M. Razler, Y. Hsiao, F. Qian, R. Fu, R. K. Khan, W. Doubleday, J. Org. Chem., 2009, 74, SI - 2
3 Chem. Name 4-nitro-1,1'-biphenyl (3a) Lit. Ref. RSC Adv., 2012, 2, 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, 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 C Elemental Analysis: Calc.: C, 72.35; H, 4.55; N, Found: C, 72.40; H, 4.65; N, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz m m d d C NMR (100.6 MHz, CDCl 3 ) δ : 124.2, 127.5, 127.9, 129.0, 129.3, 138.9, 147.2, 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
4 Chem. Name 4-nitro-1,1'-biphenyl (3a) Lit. Ref. RSC Adv., 2012, 2, 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, 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 C Elemental Analysis: Calc.: C, 72.35; H, 4.55; N, Found: C, 72.42; H, 4.67; N, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz m m d d C NMR (100.6 MHz, CDCl 3 ) δ : 124.2, 127.5, 127.9, 129.0, 129.3, 138.9, 147.2, 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
5 Chem. Name 1,1'-biphenyl (3b) Lit. Ref. Eur. J. Org. Chem. 2013, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 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 C Elemental Analysis: Calc.: C, 93.46; H, Found: C, 93.50; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 127.3, 127.4, 128.9, GC-EIMS (m/z, %): 155 (13), 154 (M +, 100), 153 (40), 152 (29), 76 (11) SI - 5
6 Chem. Name 1,1'-biphenyl (3b) Lit. Ref. Eur. J. Org. Chem., 2013, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 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 C Elemental Analysis: Calc.: C, 93.46; H, Found: C, 93.51; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 127.3, 127.4, 128.9, GC-EIMS (m/z, %): 155 (13), 154 (M +, 100), 153 (40), 152 (29), 76 (11) SI - 6
7 Chem. Name 4-methyl-1,1'-biphenyl (3c) Lit. Ref. RSC Adv., 2012, 2, 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, 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 C Elemental Analysis: Calc.: C, 92.81; H, Found: C, 92.75; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s m m m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 21.2, , , 128.8, 129.6, 137.1, 138.4, GC-EIMS (m/z, %): 169 (14), 168 (M +, 100), 167 (66), 165 (28), 153 (15), 152 (21), 115 (11) SI - 7
8 Chem. Name 4-methyl-1,1'-biphenyl (3c) Lit. Ref. RSC Adv., 2012, 2, 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, 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 C Elemental Analysis: Calc.: C, 92.81; H, Found: C, 92.74; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s m m m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 21.2, , , 128.8, 129.6, 137.1, 138.4, GC-EIMS (m/z, %): 169 (14), 168 (M +, 100), 167 (66), 165 (28), 153 (15), 152 (21), 115 (11) SI - 8
9 Chem. Name 1-phenylnaphthalene (3d) Lit. Ref. Eur. J. Org. Chem., 2013, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 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 C Elemental Analysis: Calc.: C, 94.08; H, Found: C, 94.15; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 125.5, 125.9, , , 127.0, 127.3, 127.7, , , 130.2, 131.7, 133.9, 140.4, GC-EIMS (m/z, %): 204 (M +, 100), 203 (98), 202 (61), 201 (13), 200 (13), 101 (16) SI - 9
10 Chem. Name 1-([1,1'-biphenyl]-4-yl)ethanone (3e) Lit. Ref. RSC Adv., 2012, 2, 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, 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 C Elemental Analysis: Calc.: C, 85.68; H, Found: C, 85.78; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s m m m d d 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, GC-EIMS (m/z, %): 196 (M +, 48), 182 (14), 181 (100), 153 (42), 152 (69), 151 (21), 76 (11), 43 (12) SI - 10
11 Chem. Name 1-([1,1'-biphenyl]-3-yl)ethanone (3f) Lit. Ref. Synthesis, 2013, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 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 C Elemental Analysis: Calc.: C, 85.68; H, Found: C, 85.80; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s m m m m d d s 13 C NMR (100.6 MHz, CDCl 3 ) δ : 26.9, 127.1, , , 127.9, 129.0, 129.2, 131.9, 137.8, 140.3, 141.9, GC-EIMS (m/z, %): 196 (M +, 66), 182 (14), 181 (100), 153 (68), 152 (82), 151 (25), 76 (13), 43 (19) SI - 11
12 Chem. Name 4-methoxy-1,1'-biphenyl (3g) Lit. Ref. RSC Adv., 2012, 2, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(phenyl)silane (2a) (368 mg, 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 C Elemental Analysis: Calc.: C, 84.75; H, Found: C, 84.87; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d m m 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, GC-EIMS (m/z, %): 185 (14), 184 (M +, 100), 169 (51), 141 (61), 139 (17), 115 (53) SI - 12
13 Chem. Name 4-methoxy-1,1'-biphenyl (3g) Lit. Ref. RSC Adv., 2012, 2, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 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 C Elemental Analysis: Calc.: C, 84.75; H, Found: C, 84.88; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d m m 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, GC-EIMS (m/z, %): 185 (14), 184 (M +, 100), 169 (51), 141 (61), 139 (17), 115 (53) SI - 13
14 Chem. Name 4-methoxy-1,1'-biphenyl (3g) Lit. Ref. RSC Adv., 2012, 2, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 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 C Elemental Analysis: Calc.: C, 84.75; H, Found: C, 84.86; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d m m 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, GC-EIMS (m/z, %): 185 (14), 184 (M +, 100), 169 (51), 141 (61), 139 (17), 115 (53) SI - 14
15 Chem. Name 4-methoxy-4'-methyl-1,1'-biphenyl (3h) Lit. Ref. Chem. Lett., 2011, 40, 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, 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 C Elemental Analysis: Calc.: C, 84.81; H, Found: C, 84.75; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s s d d d 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, 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
16 Chem. Name 4-methoxy-4'-methyl-1,1'-biphenyl (3h) Lit. Ref. Chem. Lett., 2011, 40, 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, 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 C Elemental Analysis: Calc.: C, 84.81; H, Found: C, 84.77; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s s d d d 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, 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
17 Chem. Name 4,4'-dimethoxy-1,1'-biphenyl (3i) Lit. Ref. Organometallics, 2008, 27, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 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 C Elemental Analysis: C, 78.48; H, Found: C, 78.44; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d d 8 13 C NMR (100.6 MHz, CDCl 3 ) δ : 55.5, 114.3, 127.9, 133.6, 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
18 Chem. Name 4-methoxy-4'-nitro-1,1'-biphenyl (3j) Lit. Ref. Organometallics, 2008, 27, 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, 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 C Elemental Analysis: Calc.: C, 68.11; H, 4.84; N, Found: C, 68.21; H, 4.90; N, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d d d 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, 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
19 Chem. Name 4-methoxy-4'-nitro-1,1'-biphenyl (3j) Lit. Ref. Organometallics, 2008, 27, 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, 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 C Elemental Analysis: Calc.: C, 68.11; H, 4.84; N, Found: C, 68.19; H, 4.80; N, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d d d 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, 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
20 Chem. Name 1-(4-methoxyphenyl)naphthalene (3k) Lit. Ref. Eur. J. Org. Chem., 2012, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 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 C Elemental Analysis: Calc.: C, 87.15; H, Found: C, 87.45; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s d m m 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, 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
21 Chem. Name 1-(4'-methoxy-[1,1'-biphenyl]-4-yl)ethanone (3l) Lit. Ref. RSC Adv., 2012, 2, 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, 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 C Elemental Analysis: Calc.: C, 79.62; H, Found: C, 79.71; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s s d d d 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, 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
22 Chem. Name 1-(4'-methoxy-[1,1'-biphenyl]-3-yl)ethanone (3m) Lit. Ref. J. Org. Chem., 2009, 74, 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, ml, 1 mmol), were consecutively added and the resulting mixture was degassed with argon. Then triethoxy(4-methoxyphenyl)silane (2b) (418 mg, 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 C Elemental Analysis: Calc.: C, 79.62; H, Found: C, 79.69; H, H NMR 400 MHz CDCl 3 δ value No. H Mult. j value/hz s s d m m d d 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, 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
23 nitro 1,1 biphenyl (3a) ppm SI - 23
24 ppm SI - 24
25 ,1 biphenyl (3b) ppm SI - 25
26 ,1 biphenyl (3b) ppm SI - 26
27 methyl 1,1 biphenyl ( ) ppm SI - 27
28 methyl 1,1 biphenyl ( ) ppm SI - 28
29 phenylnaphthalene ( ) ppm SI - 29
30 phenylnaphthalene ( ) ppm SI - 30
31 ([1,1 biphenyl] 4 yl)ethanone (3e) ppm SI - 31
32 ([1,1 biphenyl] 4 yl)ethanone (3e) ppm SI - 32
33 ([1,1 biphenyl] 3 yl)ethanone ( ) ppm SI - 33
34 ([1,1 biphenyl] 3 yl)ethanone ( ) ppm SI - 34
35 methoxy 1,1 biphenyl (3g) ppm SI - 35
36 methoxy 1,1 biphenyl (3g) ppm SI - 36
37 methoxy 4 methyl 1,1 biphenyl ( ) ppm SI - 37
38 methoxy 4 methyl 1,1 biphenyl ( ) ppm SI - 38
39 ,4 dimethoxy 1,1 biphenyl ( ) ppm SI - 39
40 ,4 dimethoxy 1,1 biphenyl ( ) ppm SI - 40
41 methoxy 4 nitro 1,1 biphenyl ( ) ppm SI - 41
42 methoxy 4 nitro 1,1 biphenyl ( ) ppm SI - 42
43 (4 methoxyphenyl)naphthalene ( ) ppm SI - 43
44 (4 methoxyphenyl)naphthalene ( ) ppm SI - 44
45 (4 methoxy [1,1 biphenyl] 4 yl)ethanone ( ) ppm SI - 45
46 (4 methoxy [1,1 biphenyl] 4 yl)ethanone ( ) ppm SI - 46
47 (4 methoxy [1,1 biphenyl] 3 yl)ethanone ( ) ppm SI - 47
48 (4 methoxy [1,1 biphenyl] 3 yl)ethanone ( ) ppm SI - 48
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