Amide bond formation via C(sp3)–H bond functionalization and CO insertion

Chemical Communications

Volumn 50, Issue 3, 2014, Pages 341-343

  Liu, Huizhen ^a   Laurenczy, Gabor ^a   Yan, Ning ^a   Dyson, Paul J ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANES; AMIDES; ANILINE COMPOUNDS; CARBON; CATALYSIS; HYDROGEN; KETONES; OXIDATION-REDUCTION; PALLADIUM; QUANTUM THEORY;

ALKANE; AMIDE; CARBON MONOXIDE; PALLADIUM; TRANSITION ELEMENT;

AMIDATION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84889250397     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc47015f     Document Type: Article

References (41)

1. T. Cupido, J. T. Puche, J. Spengler, F. Albericio, Curr. Opin. Drug Discovery Dev., 2007, 10, 768.
2. J. W. Bode, Curr. Opin. Drug Discovery Dev., 2006, 9, 765.
3. J. M. Humphrey, A. R. Chamberlin, Chem. Rev., 1997, 97, 2243.
4. C. Singh, V. Kumar, U. Sharma, N. Kumar, B. Singh, Curr. Org. Synth., 2013, 10, 241.
5. V. R. Pattabiraman, J. W. Bode, Nature, 2011, 480, 471.
6. C. L. Allen, J. M. Williams, J. Chem. Soc. Rev., 2011, 40, 3405.
7. C. Gunanathan, Y. B. David, D. Milstein, Science, 2011, 317, 790.
8. A. Brennfhrer, H. Neumann, M. Beller, Angew. Chem., Int. Ed., 2009, 48, 4114.
9. C. E. Houlden, M. Hutchby, C. D. Bailey, J. G. Ford, N. G. Simon, M. R. Tyler, G. C. Gag, K. I. L. Jones, B. Milburn, Angew. Chem., Int. Ed., 2009, 48, 1830.
10. R. Giri, J. Q. Yu, J. Am. Chem. Soc., 2008, 130, 14082.
11. S. Inoue, H. Shiota, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc., 2009, 131, 6898.
12. R. Lang, L. J. Shi, D. F. Li, C. G. Xia, F. W. Li, Org. Lett., 2012, 14, 16, 4130.
13. A. Takacs, A. Czompa, G. Krajsovszky, P. Matyus, L. Kollar, Tetrahedron, 2012, 68, 7855.
14. B. Gabriele, G. Salerno, L. Veltri, M. Costa, J. Organomet. Chem., 2001, 622, 84.
15. Y. Izawa, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn., 2004, 77, 2033.
16. S. I. Lee, S. U. Son, Y. K. Chung, Chem. Commun., 2002, 1310.
17. J. R. Martinelli, D. A. Watson, D. M. M. Freckmann, T. E. Barder, S. L. Buchwald, J. Org. Chem., 2008, 73, 7102.
18. H. Zhang, R. Y. Shi, A. X. Ding, L. J. Lu, B. Chen, A. W. Lei, Angew. Chem., Int. Ed., 2012, 51, 12542.
19. D. D. Liang, Z. W. Hu, J. L. Peng, J. B. Huang, Q. Zhu, Chem. Commun., 2013, 49, 173.
20. K. D. Hesp, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc., 2011, 133, 11430.
21. Y. Du, T. K. Hyster, T. Rovis, Chem. Commun., 2011, 47, 12074.
22. K. Muralirajan, K. Parthasarathy, C. H. Cheng, Org. Lett., 2012, 14, 4262.
23. J. Tsuji, Palladium Reagents and Catalysts, 2003
24. B. Mandy-Nicole (née Gensow), F. Zoraida, Piet W. N. M. van Leeuwen, Chem. Soc. Rev., 2009, 38, 1099.
25. P. Xie, Y. J. Xie, B. Qian, H. Zhou, C. G. Xia, H. M. Huang, J. Am. Chem. Soc., 2012, 134, 9902.
26. F. M. Miloserdov, V. V. Grushin, Angew. Chem., Int. Ed., 2012, 51, 3668.
27. J. J. Yin, S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043.
28. H. J. Chen, C. B. Cai, X. H. Liu, X. W. Li, H. F. Jiang, Chem. Commun., 2011, 47, 12224.
29. H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Direct Synthesis of Carbonyl Compounds, Plenum Press, New York, 1991
30. M. Beller, Carbonylation of Benzyl- and Aryl-X Compounds, In, Applied Homogeneous Catalysis with Organometallic Compounds, ed. B. Cornils and W. A Herrmann, 2nd edn, Wiley-VCH, Weinheim, 2002
31. L. Kollár, Modern carbonylation methods, Wiley-VCH, Verlag GmbH & Co. KgaA, Weinheim, 2008
32. C. F. J. Barnard, Organometallics, 2008, 27, 5402.
33. A. Brennfuhrer, H. Neumann, M. Beller, Angew. Chem., Int. Ed., 2009, 48, 4114.
34. X. F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev., 2011, 40, 4986.
35. F. Estevan, A. García-Bernabé, P. Lahuerta, M. Sanau, M. A. Ubeda, J. R. Galan-Mascaros, J. Organomet. Chem., 2000, 596, 248.
36. C. E. Housecroft, B. A. M. Shaykh, A. L. Rheingold, B. S. Haggerty, Acta Crystallogr., Sect. C, 1990, 46, 1549.
37. M. Tromp, J. A. van Bokhoven, G. P. F. van Strijdonck, P. W. N. M. van Leeuwen, D. C. Koningsberger, D. E. Ramaker, J. Am. Chem. Soc., 2004, 127, 777.
38. E. Burello, G. Rothenberg, Adv. Synth. Catal., 2005, 347, 1969.
39. T. M. Konrad, J. A. Fuentes, A. M. Z. Slawin, M. L. Clarke, Angew. Chem., Int. Ed., 2010, 49, 9917.
40. Y. R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, Boca Raton, FL, 2002.
41. L. Boisvert, M. C. Denney, S. K. Hanson, K. I. Goldberg, J. Am. Chem. Soc., 2009, 131, 1580.