Aerobic cross-dehydrogenative coupling of terminal alkynes and tertiary amines by a combined catalyst of Zn 2+ and OMS- 2

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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) for Aerobic cross-dehydrogenative coupling of terminal alkynes and tertiary amines by a combined catalyst of Zn 2+ and OMS- 2 Xiongjie Jin, Kazuya Yamaguchi and oritaka Mizuno* Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo tmizuno@mail.ecc.u-tokyo.ac.jp Full experimental details Instruments and reagents: GC analyses were performed on Shimadzu GC-2014 with a FID detector equipped with a Rxi-5 Sil capillary column. GC-MS spectra were recorded on Shimadzu GCMS-QP2010 equipped with a InertCap 5 capillary column at an ionization voltage of 70 ev. Liquid-state MR spectra were recorded on JEOL JM- ECA H and 13 C MR spectra were measured at and MHz, respectively, using tetramethylsilane (TMS) as an internal reference (δ = 0 ppm). OMS- 2 (BET surface area: 90 m 2 g 1 ) S1 was prepared according to the literature procedures. Activated MnO 2 (Cat. o G, for organic oxidations, Aldrich), β-mno 2 (BET surface area: 36 m 2 g 1, Cat. o , Wako) were commercially available. Solvents and substrates were obtained from Kanto Chemical, TCI, Wako, or Aldrich (reagent grade), and purified prior to the use (if required). S2 A typical procedure for CDC of terminal alkynes and tertiary amines: Into a Pyrex glass reactor (volume: ca. 20 ml) were successively placed ZnBr 2 (11.3 mg, 0.05 mmol), OMS-2 (100 mg), 1 (1 mmol), 2 (2 mmol), CPME (2 ml), and a Tefloncoated magnetic stir bar, and the reaction mixture was purged with oxygen gas, and then vigorously stirred at 100 C. After the reaction was completed, an internal standard (diphenyl) was added to the reaction mixture, and the conversions of 1 and 2 and the product yield were determined by GC analysis. As for isolation of propargylamine 1

2 products, an internal standard was not added. After the reaction, OMS-2 was filtered off (>97 % recovery), and then the filtrate was concentrated by evaporation of CPME. The crude product was subjected to column chromatography on silica gel (typically using n- hexane/diethylether as the eluent), giving the pure propargylamines. The products were identified by GC-MS and MR ( 1 H and 13 C) analyses. Reuse of OMS-2: The CDC of 1a and 2a was carried out with fresh OMS-2 as abovedescribed experimental procedure. After the reaction, OMS was retrieved by filtration, washed with acetone and water, and then calcined at 300 C for 2 h. Into a Pyrex glass reactor (volume: ca. 20 ml) were successively placed ZnBr 2 (11.3 mg, 0.05 mmol), the retrieved OMS-2 (100 mg), 1a (1 mmol), 2a (2 mmol), CPME (2 ml), and a Tefloncoated magnetic stir bar, and the reaction mixture was purged with oxygen gas, and then vigorously stirred at 100 C for 8 h. After the reaction was completed, an internal standard (diphenyl) was added to the reaction mixture, and the conversions of 1a and 2a and the yield of 3aa were determined by GC analysis. The reuse experiments were repeated 3 times. Additional references S1 R.. DeGuzman, Y.-F. Shen, E. J. eth, S. L. Suib, C.-L. O'Young, S. Levine and J. M. ewsam, Chem. Mater., 1994, 6, 815. S2 Purification of Laboratory Chemicals, 3rd ed. (Eds.: D. D. Perrin and W. L. F. Armarego), Pergamon Press, Oxford, Spectral data of propargylamines 2

3 3aa -methyl--(3-phenylprop-2-yn-1-yl)cyclohexanamine (3aa): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.63 (s, 2H), (m, 3H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.67, 26.23, 29.96, 38.68, 43.82, 61.16, 84.92, 85.80, , , , MS (EI): m/z (%) : 227 (11) [M + ], 184 (19), 171 (29), 170 (35), 116 (33), 115 (100), 94 (43), 89 (11), 82 (10), 70 (21), 68 (27), 55 (18). 3ba -methyl--(3-(o-tolyl)prop-2-yn-1-yl)cyclohexanamine (3ba): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 7H), 3.70 (s, 2H), (m, 1H), (m, 2H), 7.39 (t, J = 7.5 Hz, 1H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 21.02, 25.63, 26.22, 30.16, 38.90, 44.00, 60.92, 83.91, 89.48, , , , , , MS (EI): m/z (%) : 241 (29) [M + ], 240 (12), 199 (11), 198 (42), 185 (63), 184 (64), 170 (16), 158 (11), 150 (15), 130 (18), 129 (100), 128 (95), 127 (38), 115 (19), 104 (25), 94 (68), 77 (11), 68 (15), 55 (17). 3ca -methyl--(3-(m-tolyl)prop-2-yn-1-yl)cyclohexanamine (3ca): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), 2.32 (s, 3H), (m, 4H), 3.63 (s, 2H), 7.09 (d, J = 7.5 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 21.30, 25.65, 26.23, 29.98, 38.68, 43.81, 61.10, 85.08, 85.34, , , , , , MS (EI): m/z (%) : 241 (24) [M + ], 198 (31), 185 (52), 184 (61), 158 (11), 150 (12), 130 (22), 129 (100), 128 (35), 127 (16), 115 (18), 94 (76), 68 (14), 55 (13). 3

4 3da -methyl--(3-(p-tolyl)prop-2-yn-1-yl)cyclohexanamine (3da): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), 2.33 (s, 3H), (m, 4H), 3.61 (s, 2H), 7.09 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 21.50, 25.66, 26.22, 29.93, 38.64, 43.82, 61.13, 84.95, 84.98, , , , MS (EI): m/z (%) : 241 (23) [M + ], 198 (26), 185 (46), 184 (56), 170 (10), 158 (11), 150 (10), 130 (19), 129 (100), 128 (36), 127 (16), 115 (14), 94 (70), 68 (11), 55 (12). MeO 3ea -(3-(3-methoxyphenyl)prop-2-yn-1-yl)--methylcyclohexanamine (3ea): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.62 (s, 2H), 3.79 (s, 3H), 6.85 (ddd, J = 8.5, 2.5 and 1.0 Hz, 1H), 6.96 (dd, J = 2.5 and 1.5 Hz, 1H), 7.02 (dt, J = 7.5 and 1.0 Hz, 1H), 7.20 (t, J = 8.0 Hz, 1H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.66, 26.22, 29.94, 38.68, 43.80, 55.34, 61.18, 84.81, 85.72, , , , , , MS (EI): m/z (%) : 257 (37) [M + ], 256 (12), 215 (10), 214 (34), 201 (66), 200 (68), 174 (12), 150 (16), 146 (27), 145 (98), 115 (24), 107 (10), 103 (15), 102 (25), 95 (10), 94 (100), 77 (10), 68 (18), 55 (17). F 3fa -(3-(4-fluorophenyl)prop-2-yn-1-yl)--methylcyclohexanamine (3fa): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.61 (s, 2H), 6.98 (tt, J = 8.5 and 2.0 Hz, 2H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.65, 26.22, 29.91, 38.63, 43.76, 61.23, 83.79, 85.54, (d, J = 21.6 Hz), (d, J = 3.5 Hz), (d, J = 8.3 Hz), (d, J = Hz). MS (EI): m/z (%) : 245 (16) [M + ], 202 (22), 189 (37), 188 (46), 134 (20), 133 (100), 94 (51), 68 (12), 55 (11). 4

5 Cl 3ga -(3-(4-chlorophenyl)prop-2-yn-1-yl)--methylcyclohexanamine (3ga): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.61 (s, 2H), 7.26 (dt, J = 8.5 and 2.0 Hz, 2H), 7.34 (dt, J = 9.0 and 2.0 Hz, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.63, 26.20, 29.89, 38.64, 43.78, 61.24, 83.77, 86.98, , , , MS (EI): m/z (%) : 261 (21) [M + ], 220 (11), 218 (32), 207 (18), 206 (26), 205 (52), 204 (62), 178 (10), 170 (14), 152 (10), 151 (35), 150 (33), 149 (100), 115 (27), 114 (27), 113 (13), 94 (100), 68 (17), 55 (20), Br 3ha -(3-(4-bromophenyl)prop-2-yn-1-yl)--methylcyclohexanamine (3ha): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.60 (s, 2H), 7.27 (dt, J = 8.5 and 2.0 Hz, 2H), 7.42 (dt, J = 9.0 and 2.0 Hz, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.64, 26.21, 29.90, 38.65, 43.80, 61.26, 83.85, 87.22, , , , MS (EI): m/z (%) : 307 (19), 306 (9) [M + ], 305 (20), 264 (23), 262 (23), 251 (45), 250 (52), 249 (47), 248 (48), 196 (16), 195 (53), 194 (15), 193 (53), 183 (10), 182 (12), 170 (17), 169 (12), 150 (18), 115 (36), 114 (42), 113 (16), 94 (100), 88 (12), 70 (10), 68 (22), 55 (20). 3ia -methyl--(3-(naphthalen-1-yl)prop-2-yn-1-yl)cyclohexanamine (3ia): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.80 (s, 2H), (m, 1H), (m, 1H), (m, 1H), 7.65 (dd, J = 7.0 and 1.0 Hz, 1H), 7.78 (d, J = 8.5 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 8.35 (d, J = 8.5 Hz, 1H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.63, 26.22, 30.16, 39.00, 44.14, 61.08, 83.06, 90.65, , , , 5

6 126.38, , , , , , MS (EI): m/z (%) : 277 (20) [M + ], 234 (18), 221 (31), 220 (38), 166 (19), 165 (100), 164 (20), 163 (14), 94 (41), 68 (11). F 3 C 3ja -methyl--(3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-yl)cyclohexanamine (3ja): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.64 (s, 2H), (m, 4H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.65, 26.20, 29.92, 38.68, 43.79, 61.35, 83.69, 88.77, (q, J = Hz), (q, J = 4.8 Hz), , (q, J = 98.5 Hz), MS (EI): m/z (%) : 295 (26) [M + ], 253 (13), 252 (52), 240 (11), 239 (83), 238 (90), 212 (12), 184 (16), 183 (97), 182 (13), 150 (15), 133 (19), 115 (12), 94 (100), 68 (12), 55 (17). 3ka -methyl--(3-(pyridin-3-yl)prop-2-yn-1-yl)cyclohexanamine (3ka): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.64 (s, 2H), (m, 1H), 7.70 (dt, J = 8.0 and 2.0 Hz, 1H), 8.50 (dd, J = 5.0 and 2.0 Hz, 1H), 8.66 (d, J = 1.5 Hz, 1H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 25.58, 26.14, 29.85, 38.62, 43.75, 61.26, 81.56, 89.55, , , , , MS (EI): m/z (%) : 228 (25) [M + ], 186 (12), 185 (53), 173 (11), 172 (82), 171 (89), 150 (17), 145 (14), 144 (10), 130 (12), 119 (10), 117 (35), 116 (100), 94 (100), 90 (13), 89 (46), 82 (11), 70 (15), 68 (31), 63 (28), 55 (28). S 3la -methyl--(3-(thiophen-3-yl)prop-2-yn-1-yl)cyclohexanamine (3la): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 1H), (m, 2H), (m, 2H), (m, 4H), 3.60 (s, 2H), 7.09 (dd, J = 5.0 and 1.0 Hz, 1H), 7.23 (dd, J = 5.0 and 2.8 Hz, 1H), 7.39 (d, J = 3.0 Hz, 1H). 13 C{ 1 H} MR (

7 MHz, CDCl 3, TMS): δ 25.65, 26.23, 29.90, 38.63, 43.81, 61.16, 79.87, 85.42, , , , MS (EI): m/z (%) : 233 (20) [M + ], 190 (25), 177 (45), 176 (60), 150 (17), 122 (29), 121 (100), 94 (45), 82 (10), 77 (19), 70 (12), 68 (25), 55 (20). 3ma -(3-(cyclohex-1-en-1-yl)prop-2-yn-1-yl)--methylcyclohexanamine (3ma): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 5H), (m, 2H), (m, 2H), (m, 4H), (m, 4H), 3.51 (s, 2H), (m, 1H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 21.62, 22.41, 25.60, 26.18, 29.53, 29.89, 38.49, 43.68, 60.93, 82.62, 86.70, , MS (EI): m/z (%) : 232 (10), 231 (61) [M + ], 230 (16), 202 (10), 189 (20), 188 (69), 176 (14), 175 (97), 174 (72), 160 (34), 150 (18), 148 (22), 147 (22), 146 (37), 134 (12), 133 (12), 132 (29), 120 (30), 119 (35), 118 (12), 117 (22), 115 (15), 112 (10), 108 (16), 107 (11), 105 (15), 104 (10), 103 (12), 95 (15), 94 (79), 93 (13), 92 (22), 91 (100), 87 (10), 82 (19), 81 (48), 79 (33), 78 (15), 77 (31), 70 (36), 68 (33), 67 (12), 65 (24), 57 (10), 55 (35), 53 (12), 51 (11). Cl 3na -(7-chlorohept-2-yn-1-yl)--methylcyclohexanamine (3na): 1 H MR (500.2 MHz, CDCl 3, TMS): δ (m, 5H), (m, 3H), (m, 2H), (m, 4H), 2.25 (tt, J = 7.0 and 2.0 Hz, 2H), (m, 4H), 3.36 (t, J = 2.0 Hz, 2H), 3.56 (t, J = 7.0 Hz, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 18.16, 25.67, 26.13, 26.22, 29.79, 31.69, 38.45, 43.33, 44.63, 60.97, 76.65, MS (EI): m/z (%) : 241 (15) [M + ], 206 (14), 200 (14), 198 (42), 185 (11), 184 (23), 164 (40), 150 (45), 148 (20), 122 (10), 120 (11), 109 (12), 108 (100), 107 (15), 95 (22), 94 (35), 91 (12), 82 (26), 81 (13), 79 (12), 77 (14), 70 (17), 68 (25), 67 (17), 65 (11), 55 (29), 54 (14), 53 (15). 3ab 7

8 -benzyl--methyl-3-phenylprop-2-yn-1-amine (3ab): 1 H MR (500.2 MHz, CDCl 3, TMS): δ 2.40 (s, 3H), 3.51 (s, 2H), 3.64 (s, 2H), 7.26 (tt, J = 7.0 and 2.0 Hz, 1H), (m, 5H), (m, 2H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 42.12, 45.89, 60.40, 84.60, 85.81, , , , , , , , MS (EI): m/z (%) : 235 (25) [M + ], 234 (31), 158 (43), 144 (26), 118 (10), 116 (15), 115 (100), 92 (10), 91 (60), 89 (12), 65 (16). n-bu 3ac -methyl--(3-phenylprop-2-yn-1-yl)butan-1-amine (3ac): 1 H MR (500.2 MHz, CDCl 3, TMS): δ 0.93 (t, J = 7.3 Hz, 3H), 1.36 (sext, J = 7.4 Hz, 2H), (m, 2H), 2.36 (s, 3H), (m, 2H), 3.54 (s, 2H), (m, 3H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 14.11, 20.70, 29.91, 42.08, 46.52, 55.83, 84.74, 85.27, , , , MS (EI): m/z (%) : 201 (3) [M + ], 158 (54), 116 (11), 115 (100). n-oct 3ad -methyl--(3-phenylprop-2-yn-1-yl)octan-1-amine (3ad): 1 H MR (500.2 MHz, CDCl 3, TMS): δ 0.88 (t, J = 7.0 Hz, 3H), (m, 10H), 1.49 (quin, J = 7.3 Hz, 2H), 2.36 (s, 3H), (m, 2H), 3.54 (s, 2H), (m, 3H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 14.21, 22.77, 27.62, 27.80, 29.39, 29.67, 31.97, 42.13, 46.54, 56.21, 84.77, 85.31, , , , MS (EI): m/z (%) : 257 (3) [M + ], 159 (11), 158 (86), 116 (11), 115 (100). 3ae,-diisopropyl-3-phenylprop-2-yn-1-amine (3ae): 1 H MR (500.2 MHz, CDCl 3, TMS): δ 1.15 (d, J = 6.5 Hz, 12H), 3.25 (sep, J = 6.5 Hz, 2H), 3.65 (s, 2H), (m, 3H), (m, 2H). 13 C{ 1 H} MR (125.8 MHz, CDCl 3, TMS): δ 20.79, 34.91, 48.62, 83.57, 89.20, , , , MS (EI): m/z (%) : 215 (5) [M + ], 200 (50), 116 (16), 115 (100). 8

9 3af -methyl--(3-phenylprop-2-yn-1-yl)aniline (3af): MS (EI): m/z (%) : 222 (14), 221 (81) [M + ], 220 (69), 144 (22), 116 (12), 115 (100), 106 (11), 104 (18), 89 (15), 77 (32), 63 (10), 51 (12). 9

10 Table S1 Effect of oxidants on the CDC of phenylacetylene (1a) and,dimethylcyclohexylamine (2a) a H ZnBr H 2 O oxidant 1a (1.0 mmol) 2a (2 equiv.) 3aa Entry Oxidant Conv. (%) 1a 2a Yield of 3aa (%) 1 OMS-2/O Activated MnO 2b /O 2 6 <1 1 3 β-mno 2 /O TBHP c /O a Reaction conditions: ZnBr 2 (5 mol%), oxidant (100 mg), 1a (1.0 mmol), 2a (2.0 mmol), CPME (2 ml), 100 ºC, O 2 (1 atm), 8 h. Conversion and yield were determined by GC analysis. b Commercially available. c 1.0 mmol of 70 % TBHP in water was utilized. 10

11 Table S2 Effect of solvents on the CDC of phenylacetylene (1a) and,dimethylcyclohexylamine (2a) a H ZnBr 2, OMS H 2 O solvent 1a (1.0 mmol) 2a (2 equiv.) 3aa Entry Solvent Conv. (%) 1a 2a Yield of 3aa (%) 1 Toluene PhCF Methylpyrrolidone ,-Dimethylformamide ,-Dimethylacetamide ,4-Dioxane Dimethylsulfoxide Cyclopentylmethylether Diethylcarbonate a Reaction conditions: ZnBr 2 (5 mol%), OMS-2 (100 mg), 1a (1.0 mmol), 2a (2.0 mmol), solvent (2 ml), 100 ºC, O 2 (1 atm), 8 h. Conversion and yield were determined by GC analysis. 11

12 ZnBr 2 (5 mol%), OMS-2 (100 mg) H + + H 2 O O 2 (1 atm), 100 o C CPME (2 ml) 1a (1 mmol) 2a (2 mmol) 3aa final yield at 8 h Yield of 3aa (%) fresh 1st 2nd 3rd 85% 87% 75% 72% Time (h) Fig. S1 The reaction profiles for the reuse experiments. The reaction conditions were the same as those described in Table 1. 12

13 MeO 1a 1b 1c 1d F Cl Br 1e 1f 1g 1h F 3 C S 1i 1j 1k 1l Cl 1m 1n 2a 2b 2c 2d 2e Fig. S2 Terminal alkynes and tertiary amines used in this study. 13

14 MR Spectra 14

15 15

16 16

17 17

18 MeO MeO 18

19 F F 19

20 Cl Cl 20

21 Br Br 21

22 22

23 F 3 C F 3 C 23

24 24

25 S S 25

26 26

27 Cl Cl 27

28 28

29 n-bu n-bu 29

30 n-oct n-oct 30

31 31

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