Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

Journal of the American Chemical Society

Volumn 137, Issue 18, 2015, Pages 5875-5878

  Chen, Yifeng ^a   Romaire, Justin P ^a   Newhouse, Timothy R ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CYANIDES; DEHYDROGENATION; ESTERIFICATION; ZINC;

ENOLATES; HYDRIDE ELIMINATION; PALLADIUM CATALYST; PALLADIUM-CATALYZED; REDUCTIVE ELIMINATION; UNSATURATED ESTERS;

ESTERS;

ESTER; ISOTOPE; LACTONE; NITRILE; OXIDIZING AGENT; PALLADIUM; PROPYLENE; ZINC COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEHYDROGENATION; KINETICS; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TEMPERATURE;

EID: 84929378761     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02243     Document Type: Article

References (50)

1. Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153
2. Reich, H. J.; Wollowitz, S. Org. React. 1993, 44, 1
3. Muzart, J. Eur. J. Org. Chem. 2010, 3779
4. Stahl, S. S.; Diao, T. Comp. Org. Synth. 2014, 7, 178
5. Astin, S.; Newman, A. C. C.; Riley, H. L. J. Chem. Soc., Res. 1933, 391
6. Agnello, E. J.; Laubach, G. D. J. Am. Chem. Soc. 1957, 79, 1257
7. Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596
8. Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2245
9. Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem., Int. Ed. 2002, 41, 993
10. Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem., Int. Ed. 2002, 41, 996
11. Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566
12. Diao, T.; Wadzinski, T. J.; Stahl, S. S. Chem. Sci. 2012, 3, 887
13. Diao, T.; Pun, D.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 8205
14. Izawa, Y.; Zheng, C.; Stahl, S. S. Angew. Chem., Int. Ed. 2013, 52, 3672
15. Theissen, R. J. J. Org. Chem. 1971, 36, 752
16. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011
17. Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797
18. Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423
19. Matsuo, J.-i.; Aizawa, Y. Tetrahedron Lett. 2005, 46, 407
20. Levine, R.; Sheppard, C. S. J. Org. Chem. 1974, 39, 3556
21. DiBiase, S. A.; Wolak, R. P., Jr.; Dishong, D. M.; Gokel, G. W. J. Org. Chem. 1980, 45, 3630
22. Noda, Y.; Akiba, Y.; Kashima, M. Synth. Commun. 1996, 26, 4633
23. Clarke, P. D.; Fitton, A. O.; Suschitzky, H.; Wallace, T. W. Tetrahedron Lett. 1986, 27, 91
24. Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813
25. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137
26. Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887
27. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330 and references therein
28. Tian, G.; Boyle, P. D.; Novak, B. M. Organometallics 2002, 21, 1462
29. Collum, D. B.; McNeil, A. J.; Ramirez, A. Angew. Chem., Int. Ed. 2007, 46, 3002 and references therein
30. Takacs, J. M.; Lawson, E. C.; Clement, F. J. Am. Chem. Soc. 1997, 119, 5956
31. Lloyd-Jones, G. C.; Slatford, P. A. J. Am. Chem. Soc. 2004, 126, 2690
32. Porth, S.; Bats, J. W.; Trauner, D.; Giester, G.; Mulzer, J. Angew. Chem., Int. Ed. 1999, 38, 2015
33. Trost, B. M.; Weber, L. J. Am. Chem. Soc. 1975, 97, 1611
34. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395
35. Hruszkewycz, D. P.; Balcells, D.; Guard, L. M.; Hazari, N.; Tilset, M. J. Am. Chem. Soc. 2014, 136, 7300
36. Boldrini, G. P.; Mengoli, M.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1986, 27, 4223
37. The difference in the 1H NMR and isolated yields may be the result of the formation of many minor byproducts, loss of material during purification, or a systematic error in the measurement of the 1H NMR yield.
38. Barton, D. H.; Lester, D. J.; Ley, S. V. J. Chem. Soc., Chem. Commun. 1978, 130
39. Cross, A. D. (Syntex Corp.). Neth. Pat. 6.503,543 (1965).
40. Jagdale, A. R.; Sudalai, A. Tetrahedron Lett. 2008, 49, 3790
41. Supporting Information for selected reaction conditions for the α,β-dehydrogenation of nitriles.
42. With the reported reaction conditions some functionality was not tolerated, including lactones that lack substitution at the β-position, protected amino acids, and α-aryl-substituted nitriles. Additionally, substrates were generally selected such that regioisomers could not be formed during the β-hydride elimination.
43. In order to obtain initial rate data, the catalyst loading was decreased to 0.125 mol %. See the Supporting Information for details.
44. Gómez-Gallego, M.; Sierra, M. A. Chem. Rev. 2011, 111, 4857
45. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066
46. Alexanian, E. J.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 15627
47. Abis, L.; Sen, A.; Halpern, J. J. Am. Chem. Soc. 1978, 100, 2915
48. McCarthy, T. J.; Nuzzo, R. G.; Whitesides, G. M. J. Am. Chem. Soc. 1981, 103, 3396
49. Michelin, R. A.; Faglia, S.; Uguagliati, P. Inorg. Chem. 1983, 22, 1831
50. Datta, A.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2008, 130, 2726