Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2009
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1 Supporting Information Copyright Wiley-VC Verlag Gmb & Co. KGaA, Weinheim, 2009
2 Supporting Information for Graphite-Supported Gold anoparticles as Efficient Catalyst for Aerobic xidation of Benzylic Amines to Imines and -Substituted 1,2,3,4-Tetrahydroisoquinolines to Amides: Synthetic Applications and Mechanistic Study Man-o So, Yungen Liu, Chi-Ming o, and Chi-Ming Che* Department of Chemistry and pen Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of ong Kong, Pokfulam Road, ong Kong SAR, China. Part I. List of Figures P. 2 Part II. List of Tables P. 3 Part III. Characterization of Compounds P. 4 1
3 Part I. List of Figures Figure S1. Plot of reaction rate (Ro) against oxygen partial pressure (P 2 ) on the aerobic oxidation of dibenzylamine (1a) catalyzed by AuPs/C. Reaction conditions: dibenzylamine (0.4 mmol), AuPs/C (Au: 5 mol %), toluene (5 ml), 2 ( atm) bubbling, 110 o C. 2
4 Part II. List of Tables Table S1. Listing of log k rel and σ values for the AuPs/C catalyzed aerobic oxidation of para-substituted -phenylbenzylamines. Y AuPs/C (Au: 5 mol %), 2 bubbling toluene, 1.5 h, 110 o C Y Entry Y log k rel σ 1 Me Me Cl CF
5 Part III. Characterization of Compounds: Compound Reference C. A. ewman, J. C. Antilla, P. Chen, A. V. Predeus, L. Fielding, W. D. Wulff, J. Am. Chem. Soc. 2007, 129, a Z. Zhu, J.. Espenson, J. Am. Chem. Soc. 1996, 118, b J. L. G. Ruano, J. Alemán, I. Alonso, A. Parra, V. Marcos, J. Aguirre, Chem. Eur. J. 2007, 13, c Z. Zhu, J.. Espenson, J. Am. Chem. Soc. 1996, 118, e R. Torregrosa, I. M. Pastor, M. Yus, Tetrahedron 2005, 61, Cl 2f M.. Ibrahim,. K. AL-Deeb, E-J. Chem. 2006, 3, Br 2g 2h V. Koleva, T. Dudev, I. Wawer, J. Mol. Struct. 1997, 412, M.. Ibrahim,. K. AL-Deeb, E-J. Chem. 2006, 3, i 2j Z. Zhu, J.. Espenson, J. Am. Chem. Soc. 1996, 118,
6 M. J. Tomaszewski, J. Warkentin,.. Werstiuk, Aust. J. Chem. 1995, 48, k K. C. icolaou, C. J.. Mathison, T. Montagnon, J. Am. Chem. Soc. 2004, 126, l. aeimi, F. Salimi, K. Rabiei, J. Mol. Catal. A-Chem. 2006, 260, Me a 2m 2p Me K. C. icolaou, C. J.. Mathison, T. Montagnon, J. Am. Chem. Soc. 2004, 126, K. C. icolaou, C. J.. Mathison, T. Montagnon, J. Am. Chem. Soc. 2004, 126, W. uang, J. Li, L. u, Synthetic Commun. 2007, 37, J. Almena, F. Foubelo, M. Yus, Tetrahedron 1996, 52, b C. Perrio-uard, C. Aubert, M.-C. Lasne, J. Chem. Soc., Perkin Trans , J. Kumpaty, S. Bhattacharyya, Synthesis 2005, c 14d 14f C. Perrio-uard, C. Aubert, M.-C. Lasne, J. Chem. Soc., Perkin Trans , C. Perrio-uard, C. Aubert, M.-C. Lasne, J. Chem. Soc., Perkin Trans , A. P. Venkov, S. M. Statkova-Abeghe, Tetrahedron 1996, 52, a 5
7 15c 15f K. rito, A. oribata, T. akamura,. Ushito,. agasaki, M. Yuguchi, S. Yamashita, M. Tokuda, J. Am. Chem. Soc. 2004, 126, K. rito, A. oribata, T. akamura,. Ushito,. agasaki, M. Yuguchi, S. Yamashita, M. Tokuda, J. Am. Chem. Soc. 2004, 126, A. P. Venkov, S. M. Statkova-Abeghe, Tetrahedron 1996, 52, a A. P. Venkov, S. M. Statkova-Abeghe, Tetrahedron 1996, 52, b A. P. Venkov, S. M. Statkova-Abeghe, Tetrahedron 1996, 52, f Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, Ph 17 Z. Li, C.-J. Li, Eur. J. rg. Chem. 2005, Ph Et Et 19 Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, Ph 22 Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, Ph 24 6
8 27a Me. Sharghi, M.. Beyzavi, M. M. Doroodmand, Eur. J. rg. Chem. 2008, d 27e 27f Cl Br. Sharghi, M.. Beyzavi, M. M. Doroodmand, Eur. J. rg. Chem. 2008, Sharghi, M.. Beyzavi, M. M. Doroodmand, Eur. J. rg. Chem. 2008, L.-. Du, Y.-G. Wang, Synthesis 2007, Sharghi, M.. Beyzavi, M. M. Doroodmand, Eur. J. rg. Chem. 2008, g Cl. Sharghi, M.. Beyzavi, M. M. Doroodmand, Eur. J. rg. Chem. 2008, Cl 27h D. Mizuno, K. Yamaguchi, Catal. Today 2008, 132,
9 2d -(4-tert-butylbenzylidene)benzenamine (2d) Yellow oil. 1 MR (300 Mz, CDCl 3, 25 o C, TMS): δ = 8.42 (s, 1), 7.84 (d, 3 J(,) = 8.4 z, 2), 7.49 (d, 3 J(,) = 8.4 z, 2), 7.38 (m, 2), 7.21 (m, 3), 1.35 ppm (s, 9); 13 C MR (75 Mz, CDCl 3, 25 o C): δ = 160.7, 130.1, 129.5, 129.1, 126.4, 126.2, 126.1, 121.3, 35.4, 31.6 ppm; MS (EI) m/z 237 (M + ); RMS (EI) m/z for C (M + ), calcd , found n -(4-nitrobenzylidene)cyclohexanamine (2n) Yellow Solid. 1 MR (300 Mz, CDCl 3, 25 o C, TMS): δ = 8.39 (s, 1), 8.25 (d, 3 J(,) = 8.7 z, 2), 7.89 (d, 3 J(,) = 8.7 z, 2), (m, 1), (m, 7), ppm (m, 3); 13 C MR (75 Mz, CDCl 3, 25 o C): δ = 156.6, 149.2, 142.6, 129.1, 124.2, 70.5, 34.6, 25.97, ppm; MS (EI) m/z 232 (M + ); RMS (EI) m/z for C (M + ), calcd , found o -(4-methoxybenzylidene)cyclohexanamine (2o) Colourless liquid. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.24 (s, 1), 7.66 (d, 3 J(,) = 8.7 z, 2), 6.91 (d, 3 J(,) = 8.7 z, 2), 3.83 (s, 3), (m, 1), (m, 2), (m, 3), (m, 2), ppm (m, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 157.9, 129.6, 113.9, 69.9, 55.3, 34.5, 25.7, 24.9 ppm; MS (EI) m/z 217 (M + ); RMS (EI) m/z for C (M + ), calcd , found
10 2q -(4-tert-butylbenzylidene)(4-tert-butylphenyl)methanamine (2q) White solid. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.36 (s, 1), 7.71 (d, 3 J(,) = 8.4 z, 2), 7.43 (d, 3 J(,) = 8.4 z, 2), 7.36 (d, 3 J(,) = 8.4 z, 2), 7.26 (d, 3 J(,) = 8.4 z, 2), 4.78 (s, 2), 1.33 (s, 9), 1.31 ppm (s, 9); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 161.7, 154.1, 149.8, 136.4, 133.6, 128.1, 127.7, 125.5, 125.4, 64.8, 34.9, 34.5, 31.4, 31.2 ppm; MS (EI) m/z 307 (M + ); RMS (EI) m/z for C (M + ), calcd , found Me 8a 6-methoxyquinoline (8a) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.64 (dd, J(,) = 4.2, 1.6 z, 1), 7.89 (d, 3 J(,) = 8.7 z, 2), 7.25 (dd, J(,) = 9.2, 2.8 z, 1), (m, 1), 6.91 (d, 3 J(,) = 2.8 z, 1), 3.78 ppm (s, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 157.7, 147.9, 144.4, 134.7, 130.8, 129.3, 122.2, 121.3, 105.1, 55.5 ppm; MS (EI) m/z 159 (M + ); RMS (EI) m/z for C (M + ), calcd , found b Quinoline (8b) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.92 (dd, J(,) = 4.2, 1.7 z, 1), (m, 2), 7.82 (m, 1), (m, 1), (m, 1), 7.40 ppm (dd, J(,) = 8.3, 4.2 z, 1); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 150.4, 148.2, 136.1, 129.5, 129.4, 128.3, 127.8, 126.6, ppm; MS (EI) m/z 129 (M + ); RMS (EI) m/z for C (M + ), calcd , found
11 8c Indole (8c) White solid. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 7.79 (brs, 1), 7.63 (d, 3 J(,) = 7.8 z, 1), 7.26 (d, 3 J(,) = 8.1 z, 1), (m, 1), (m, 1), (m, 1), ppm (m, 1); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 135.8, 127.9, 124.4, 122.1, 120.8, 119.9, 111.2, ppm; MS (EI) m/z 117 (M + ); RMS (EI) m/z for C (M + ), calcd , found & Yellow oil. 1 MR (500 Mz, CDCl 3, 25 o C, TMS): δ = (m, 1), (m, 2), (m, 3), (m, 1), 6.99 (d, 3 J(,) = 7.5 z, 1), 5.29 (s, 1), 4.52 (d, 3 J(,) = 9.6 z, 1), 4.04 (d, 3 J(,) = 9.6 z, 1), (m, 2), (m, 1), (m, 1), (m, 1), (m, 3), 2.84 (dt, J(,) = 15.8, 2.9 z, 1), 2.57 (dt, J(,) = 16.7, 3.6 z, 1), 0.86 ppm (t, 3 J(,) = 7.1 z, 3); 13 C MR (125 Mz, CDCl 3, 25 o C): δ = 173.0, 136.3, 135.7, 135.4, 132.1, , , 127.2, 127.0, 126.7, 126.6, 125.1, 82.9, 66.6, 62.4, 60.5, 46.9, 44.4, 29.4, 22.7, 13.7 ppm; MS (EI) m/z 348 (M + ); RMS (EI) m/z for C (M + ), calcd , found Yellow oil. 1 MR (500 Mz, CDCl 3, 25 o C, TMS): δ = (m, 1), (m, 2), (m, 5), 5.09 (s, 1), 4.50 (d, 3 J(,) = 8.9 z, 1), (m, 2), 3.66 (d, 3 J(,) = 9.0 z, 1), (m, 1), (m, 1), (m, 3), (m, 3), 1.37 ppm (t, 3 J(,) = 7.2 z, 3); 13 C MR (125 Mz, CDCl 3, 25 o C): δ = 174.2, 137.3, 134.8, 134.7, 132.4, 128.7, 128.4, 127.4, 126.8, , , , 79.4, 71.0, 64.9, 61.2, 49.9, 43.2, 29.5, 29.1, 14.3 ppm; MS (EI) m/z 348 (M + ); RMS (EI) m/z for C (M + ), calcd , found
12 13a 4,4-dimethyl-3,4,6,7-tetrahydro-1-pyrido[2,1-a]isoquinolin-2(11b)-one (13a) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = (m, 3), (m, 1), 4.23 (dd, 3 J(,) = 11.8, 3.4 z, 1), (m, 1), (m, 1), (m, 2), (m, 1), (m, 2), 2.25 (dd, 3 J(,) = 13.5, 2.2 z, 1), 1.37 (s, 3), 1.10 ppm (s, 3); 13 C MR (125 Mz, CDCl 3, 25 o C): δ = 209.1, 137.9, 134.6, 128.8, 126.3, 126.1, 125.7, 57.7, 56.4, 53.9, 47.5, 41.2, 30.6, 30.1, 19.7 ppm; MS (EI) m/z 229 (M + ); RMS (EI) m/z for C (M + ), calcd , found b 1-(1,2,3,4-tetrahydroisoquinolin-1-yl)hexan-2-one (13b) Yellow oil. 1 MR (500 Mz, CDCl 3, 25 o C, TMS): δ = (m, 2), (m, 1), (m, 1), 4.51 (dd, 3 J(,) = 8.5, 3.9 z, 1), (m, 1), (m, 1), (m, 3), (m, 1), (m, 2), (m, 2), (m, 2), 0.91 ppm (t, 3 J(,) = 7.3 z, 3); 13 C MR (125 Mz, CDCl 3, 25 o C): δ = 210.8, 137.9, 135.5, 129.5, 126.2, 125.9, 125.6, 52.0, 49.5, 43.4, 41.1, 29.8, 25.8, 22.3, 13.9 ppm; MS (EI) m/z 231 (M + ); RMS (EI) m/z for C (M + ), calcd , found c 1-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)ethanone (13c) Yellow oil. 1 MR (500 Mz, CDCl 3, 25 o C, TMS): δ = 7.99 (d, 3 J(,) = 7.3 z, 2), 7.57 (t, 3 J(,) = 7.4 z, 1), 7.47 (t, 3 J(,) = 7.7 z, 2), (m, 4), 4.74 (dd, 3 J(,) = 9.2, 3.2 z, 1), 3.54 (dd, J(,) = 17.6, 9.2 z, 1), 3.46 (dd, J(,) = 17.6, 3.2 z, 1), (m, 1), (m, 1), (m, 1), ppm (m, 1); 13 C MR (125 Mz, CDCl 3, 25 o C): δ = 199.4, 137.8, 137.0, 135.5, 133.3, 129.5, 128.7, 128.1, 126.3, 126.0, 125.8, 52.1, 45.5, 40.9, 29.7 ppm; MS (EI) m/z 251 (M + ); RMS (EI) m/z for C (M + ), calcd , found
13 14e 2-octyl-1,2,3,4-tetrahydroisoquinoline (14e) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = (m, 3), (m, 1), 3.62 (s, 2), 2.91 (t, 3 J(,) = 5.9 z, 2), 2.72 (t, 3 J(,) = 5.9 z, 2), 2.49 (t, 3 J(,) = 7.7 z, 2), (m, 12), 0.88 ppm (t, 3 J(,) = 6.9 z, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 128.6, 126.6, 126.0, 125.5, 58.6, 56.3, 51.0, 31.9, 29.6, 29.3, 29.1, 27.7, 27.2, 22.7, 14.1 ppm; MS (EI) m/z 245 (M + ); RMS (EI) m/z for C (M + ), calcd , found b 2-ethyl-3,4-dihydroisoquinolin-1(2)-one (15b) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.08 (dd, 3 J(,) = 7.7, 1.2 z, 1), (m, 1), (m, 1), 7.16 (d, 3 J(,) = 7.4 z, 1), 3.63 (q, 3 J(,) = 7.2 z, 2), 3.55 (t, 3 J(,) = 6.7 z, 2), 2.99 (t, 3 J(,) = 6.6 z, 2), 1.22 ppm (t, 3 J(,) = 7.2 z, 3); 13 C MR (125 Mz, CDCl 3, 25 o C): δ = 164.1, 138.0, 131.4, 128.2, 127.0, 126.8, 45.5, 42.2, 28.2, 12.8 ppm; MS (EI) m/z 175 (M + ); RMS (EI) m/z for C (M + ), calcd , found
14 15d 2-butyl-3,4-dihydroisoquinolin-1(2)-one (15d) Yellow oil. 1 MR (300 Mz, CDCl 3, 25 o C, TMS): δ = 8.04 (dd, 3 J(,) = 7.6, 1.2 z, 1), (m, 1), (m, 1), 7.12 (d, 3 J(,) = 7.3 z, 1), (m, 4), 2.93 (t, 3 J(,) = 6.6 z, 2), (m, 2), (m, 2), 0.92 ppm (t, 3 J(,) = 7.3 z, 3); 13 C MR (75 Mz, CDCl 3, 25 o C): δ = 164.1, 137.8, 131.3, 129.6, 128.0, 126.8, 126.7, 47.1, 45.9, 29.7, 28.1, 20.1, 13.8 ppm; MS (EI) m/z 203 (M + ); RMS (EI) m/z for C (M + ), calcd , found e 2-octyl-3,4-dihydroisoquinolin-1(2)-one (15e) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.08 (dd, 3 J(,) = 7.6, 1.2 z, 1), (m, 1), (m, 1), 7.16 (d, 3 J(,) = 7.4 z, 1), (m, 4), 2.97 (t, 3 J(,) = 6.6 z, 2), (m, 2), (m, 10), 0.87 ppm (t, 3 J(,) = 7.0 z, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 164.2, 137.9, 131.4, 129.7, 128.2, 126.9, 126.7, 47.5, 46.0, 31.8, 29.4, 29.2, 28.2, 27.7, 27.0, 22.6, 14.1 ppm; MS (EI) m/z 259 (M + ); RMS (EI) m/z for C (M + ), calcd , found c 2-propylisoquinolin-1(2)-one (16c) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.43 (d, 3 J(,) = 8.1 z, 1), (m, 1), (m, 2), 7.06 (d, 3 J(,) = 7.3 z, 1), 6.48 (d, 3 J(,) = 7.3 z, 1), 3.96 (t, 3 J(,) = 7.3 z, 2), (m, 2), 0.98 ppm (t, 3 J(,) = 7.5 z, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 162.1, 137.0, 132.0, 131.8, 127.8, 126.7, 125.8, 105.9, 50.9, 22.5, 11.2 ppm; MS (EI) m/z 187 (M + ); RMS (EI) m/z for C (M + ), calcd , found
15 16d 2-butylisoquinolin-1(2)-one (16d) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.44 (d, 3 J(,) = 8.1 z, 1), 7.62 (t, 3 J(,) = 7.5 z, 1), (m, 2), 7.06 (d, 3 J(,) = 7.3 z, 1), 6.49 (d, 3 J(,) = 7.3 z, 1), 4.01 (t, 3 J(,) = 7.4 z, 2), (m, 2), (m, 2), 0.96 ppm (t, 3 J(,) = 7.4 z, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 162.2, 137.1, 132.1, 131.8, 127.9, 126.8, 125.9, 106.0, 49.3, 31.5, 20.1, 13.9 ppm; MS (EI) m/z 201 (M + ); RMS (EI) m/z for C (M + ), calcd , found e 2-octylisoquinolin-1(2)-one (16e) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 8.44 (d, 3 J(,) = 8.1 z, 1), 7.62 (t, 3 J(,) = 7.5 z, 1), (m, 2), 7.06 (d, 3 J(,) = 7.3 z, 1), 6.49 (d, 3 J(,) = 7.3 z, 1), 3.99 (t, 3 J(,) = 7.4 z, 2), (m, 2), (m, 10), 0.87 ppm (t, 3 J(,) = 6.8 z, 3); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 162.3, 137.1, 132.1, 131.8, 127.9, 126.8, 125.9, 106.0, 49.6, 31.9, 29.43, 29.38, 29.3, 26.9, 22.7, 14.2 ppm; MS (EI) m/z 257 (M + ); RMS (EI) m/z for C (M + ), calcd , found Ph CF phenyl-1-(2-(4-(trifluoromethyl)phenyl)ethynyl)-1,2,3,4-tetrahydroisoquinoline (21) Yellow oil. 1 MR (400 Mz, CDCl 3, 25 o C, TMS): δ = 7.45 (d, 3 J(,) = 7.9 z, 2), (m, 5), (m, 3), 7.11 (d, 3 J(,) = 7.5 z, 2), (m, 1), 5.65 (s, 1), (m, 1), (m, 1), (m, 1), ppm (m, 1); 13 C MR (100 Mz, CDCl 3, 25 o C): δ = 149.5, 134.9, 134.5, 132.1, 129.3, 129.1, , , 126.5, , , , , 120.0, 116.8, 91.4, 83.6, 52.5, 43.5, 29.0 ppm; MS (EI) m/z 377 (M + ); RMS (EI) m/z for C F 3 1 (M + ), calcd , found
16 27b Me Me 2-(3,4-dimethoxyphenyl)-1-benzimidazole (27b) White solid. 1 MR (400 Mz, CD 3 D, 25 o C, TMS): δ = 7.65 (d, 3 J(,) = 2.0 z, 1), 7.59 (dd, J(,) = 8.38, 1.0 z, 1), (m, 2), (m, 2), 7.01 (d, 3 J(,) = 8.4 z, 1), 3.88 (s, 3), 3.82 ppm (s, 3); 13 C MR (100 Mz, CD 3 D, 25 o C): δ = 153.5, 152.4, 150.8, 123.7, 120.9, 112.8, 111.2, 56.49, ppm; MS (EI) m/z 254 (M + ); RMS (EI) m/z for C (M + ), calcd , found c 2-mesityl-1-benzimidazole (27c) White solid. 1 MR (400 Mz, CD 3 D, 25 o C, TMS): δ = 7.51 (brs, 2), (m, 2), 6.92 (s, 2), 2.26 (s, 3), 2.03 ppm (s, 6); 13 C MR (100 Mz, CD 3 D, 25 o C): δ = 153.5, 140.7, 138.9, 129.4, 129.2, 123.5, 21.3, 19.9 ppm; MS (EI) m/z 236 (M + ); RMS (EI) m/z for C (M + ), calcd , found
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