Dual role of carboxylic acid additive: Mechanistic studies and implication for the asymmetric C-H amidation Dedicated to Professor Yoshiaki Nakao on his receipt of the Tetrahedron Young Investigator Award

Tetrahedron

Volumn 71, Issue 26-27, 2015, Pages 4504-4511

  Gwon, Donghyeon ^a,b   Park, Sehoon ^a,b   Chang, Sukbok ^a,b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Institute for Basic Science   (South Korea)

Author keywords

Acid additive effects; Asymmetric induction; C H amidation; Mechanistic study; Phosphoryl compounds

Indexed keywords

CARBOXYLIC ACID; IRIDIUM COMPLEX; SILVER;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; HEATING; HYDROGEN BOND; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84930085627     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.02.065     Document Type: Article

References (64)

1. D.A. Colby, R.G. Bergman, and J.A. Ellman Chem. Rev. 110 2010 624
2. T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147
3. G. Song, F. Wang, and X. Li Chem. Soc. Rev. 41 2012 3651
4. I.P. Beletskaya, and A.V. Cheprakov Organometallics 31 2012 7753
5. P.B. Arockiam, C. Bruneau, and P.H. Dixneuf Chem. Rev. 112 2012 5879
6. G. Rouquet, and N. Chatani Angew. Chem., Int. Ed. 52 2013 11726
7. E.M. Beccalli, G. Broggini, M. Martinelli, and S. Sottocornola Chem. Rev. 107 2007 5318
8. X. Chen, C.E. Goodhue, and J.-Q. Yu J. Am. Chem. Soc. 128 2006 12634
9. X. Chen, J.-J. Li, X.-S. Hao, C.E. Goodhue, and J.-Q. Yu J. Am. Chem. Soc. 128 2006 78
10. D. Shabashov, and O. Daugulis J. Am. Chem. Soc. 132 2010 3965
11. J.C. Lewis, R.G. Bergman, and J.A. Ellman J. Am. Chem. Soc. 129 2007 5332
12. R.D. Baxter, D. Sale, K.M. Engle, J.-Q. Yu, and D.G. Blackmond J. Am. Chem. Soc. 134 2012 4600
13. K.M. Engle, T.-S. Mei, M. Wasa, and J.-Q. Yu Acc. Chem. Res. 45 2012 788
14. J. Ryu, S.H. Cho, and S. Chang Angew. Chem., Int. Ed. 51 2012 3677
15. S.H. Cho, S.J. Hwang, and S. Chang J. Am. Chem. Soc. 130 2008 9254
16. K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 129 2007 11904
17. J. Wencel-Delord, C. Nimphius, H. Wang, and F. Glorius Angew. Chem., Int. Ed. 51 2012 13001
18. D.R. Stuart, and K. Fagnou Science 316 2007 1172
19. R. Shang, L. Ilies, A. Matsumoto, and E. Nakamura J. Am. Chem. Soc. 135 2013 6030
20. S.H. Cho, J.Y. Kim, J. Kwak, and S. Chang Chem. Soc. Rev. 40 2011 5068
21. T. Kawano, K. Hirano, T. Satoh, and M. Miura J. Am. Chem. Soc. 132 2010 6900
22. W.C.P. Tsang, N. Zhang, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 14560
23. A.R. Dick, K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 126 2004 2300
24. X.-F. Cheng, Y. Li, Y.-M. Su, F. Yin, J.-Y. Wang, J. Sheng, H.U. Vora, X.-S. Wang, and J.-Q. Yu J. Am. Chem. Soc. 135 2013 1236
25. V.S. Thirunavukkarasu, and L. Ackermann Org. Lett. 14 2012 6206
26. K.L. Hull, W.Q. Anani, and M.S. Sanford J. Am. Chem. Soc. 128 2006 7134
27. X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, and Z.-J. Shi J. Am. Chem. Soc. 128 2006 7416
28. R. Giri, X. Chen, and J.-Q. Yu Angew. Chem., Int. Ed. 44 2005 2112
29. R.B. Bedford, M.F. Haddow, C.J. Mitchell, and R.L. Webster Angew. Chem., Int. Ed. 50 2011 5524
30. L. Ackermann Chem. Rev. 111 2011 1315
31. L. Ackermann Acc. Chem. Res. 47 2014 281
32. D. Lapointe, and K. Fagnou Chem. Lett. 39 2010 1118
33. A. Maleckis, J.W. Kampf, and M.S. Sanford J. Am. Chem. Soc. 135 2013 6618
34. M. Schinkel, I. Marek, and L. Ackermann Angew. Chem., Int. Ed. 52 2013 3977
35. K.J.T. Carr, D.L. Davies, S.A. Macgregor, K. Singh, and B. Villa-Marcos Chem. Sci. 5 2014 2340
36. G.C. Kuang, H.A. Michaels, J.T. Simmons, R.J. Clark, and L. Zhu J. Org. Chem. 75 2010 6540
37. Y. Li, X.-S. Zhang, H. Li, W.-H. Wang, K. Chen, B.-J. Li, and Z.-J. Shi Chem. Sci. 3 2012 1634
38. H. Hwang, J. Kim, J. Jeong, and S. Chang J. Am. Chem. Soc. 136 2014 10770
39. D. Gwon, D. Lee, J. Kim, S. Park, and S. Chang Chem. - Eur. J. 20 2014 12421
40. H. Onouchi, T. Miyagawa, A. Furuko, K. Maeda, and E. Yashima J. Am. Chem. Soc. 127 2005 2960
41. M. Terada Synthesis 2010 1929
42. M. Koziołkiewicz, A. Maciaszek, W.J. Stec, D. Semizarov, L. Victorova, and A. Krayevsky FEBS Lett. 434 1998 77
43. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029
44. T. Ohkuma, M. Kitamura, and R. Noyori I. Ojima, Catalytic Asymmetric Synthesis 2000 Wiley-VCH Weinheim, Germany Chapter 1
45. J. Ryu, J. Kwak, K. Shin, D. Lee, and S. Chang J. Am. Chem. Soc. 135 2013 12861
46. L. Chu, X.-C. Wang, C.E. Moore, A.L. Rheingold, and J.-Q. Yu J. Am. Chem. Soc. 135 2013 16344
47. L. Chu, K.-J. Xiao, and J.-Q. Yu Science 346 2014 451
48. J. He, S. Li, Y. Deng, H. Fu, B.N. Laforteza, J.E. Spangler, A. Homs, and J.-Q. Yu Science 343 2014 1216
49. D.G. Musaev, A. Kaledin, B.-F. Shi, and J.-Q. Yu J. Am. Chem. Soc. 134 2012 1690
50. B.-F. Shi, N. Maugel, Y.-H. Zhang, and J.-Q. Yu Angew. Chem., Int. Ed. 47 2008 4882
51. M. Wasa, K.M. Engle, D.W. Lin, E.J. Yoo, and J.-Q. Yu J. Am. Chem. Soc. 133 2011 19598
52. K.-J. Xiao, D.W. Lin, M. Miura, R.-Y. Zhu, W. Gong, M. Wasa, and J.-Q. Yu J. Am. Chem. Soc. 136 2014 8138
53. M. Gómez-Gallego, and M.A. Sierra Chem. Rev. 111 2011 4857
54. E.M. Simmons, and J.F. Hartwig Angew. Chem., Int. Ed. 51 2012 3066
55. S.H. Park, J. Kwak, K. Shin, J. Ryu, Y. Park, and S. Chang J. Am. Chem. Soc. 136 2014 2492
56. T. Kang, Y. Kim, D. Lee, Z. Wang, and S. Chang J. Am. Chem. Soc. 136 2014 4141
57. J. Kim, and S. Chang Angew. Chem., Int. Ed. 53 2014 2203
58. J. Ryu, K. Shin, S.H. Park, J.Y. Kim, and S. Chang Angew. Chem., Int. Ed. 51 2012 9904
59. K. Shin, Y. Baek, and S. Chang Angew. Chem., Int. Ed. 52 2013 8031
60. K.-H. Ng, A.S.C. Chan, and W.-Y. Yu J. Am. Chem. Soc. 132 2010 12862
61. K. Sun, Y. Li, T. Xiong, J. Zhang, and Q. Zhang J. Am. Chem. Soc. 133 2011 1694
62. J.Y. Kim, S.H. Park, J. Ryu, S.H. Cho, S.H. Kim, and S. Chang J. Am. Chem. Soc. 134 2012 9110
63. L. Li, W.W. Brennessel, and W.D. Jones Organometallics 28 2009 3492
64. J. Waser, B. Gaspar, H. Nambu, and E.M. Carreira J. Am. Chem. Soc. 128 2006 11693