Commutative reduction of aromatic ketones to arylmethylenes/alcohols by hypophosphites catalyzed by Pd/C under biphasic conditions

Tetrahedron

Volumn 70, Issue 12, 2014, Pages 2088-2095

  Guyon, Carole ^a   Baron, Marc ^a   Lemaire, Marc ^a   Popowycz, Florence ^a   Métay, Estelle ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Deoxygenation; Hypophosphite; Ketones; Palladium; Reduction

Indexed keywords

ALCOHOL DERIVATIVE; AROMATIC COMPOUND; CARBENE; CARBON; HYDROGEN; KETONE DERIVATIVE; PALLADIUM; PHOSPHITE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; DEOXYGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 84896708748     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.02.014     Document Type: Article

References (61)

1. E. Clemmensen Ber. Dtsch. Chem. Ges. 46 1913 1837
2. L. Kürti, and B. Czakó Strategic Applications of Named Reactions in Organic Synthesis 2005 Elsevier Academic Amsterdam, The Netherlands 496
3. R. Mozingo, D.E. Wolf, S.A. Harris, and K.J. Folkers J. Am. Chem. Soc. 65 1943 1013
4. W.H. Hartung, and F.S. Crossley J. Am. Chem. Soc. 56 1934 158
5. P. Herold, A.F. Indolese, M. Studer, H.P. Jalett, U. Siegrist, and H.U. Blaser Tetrahedron 56 2000 6497
6. M.A. Alotaibi, E.F. Kozhevnikova, and I.V. Kozhevnikov J. Catal. 293 2012 141
7. I. Wender, H. Greenfield, and M. Orchin J. Am. Chem. Soc. 73 1951 2656
8. F. Zaccheria, N. Ravasio, M. Ercoli, and P. Allegrini Tetrahedron Lett. 46 2005 7743
9. D. Taher, M.E. Thibault, D. Di Mondo, M. Jennings, and M. Schlaf Chem. - Eur. J. 15 2009 10132
10. J. Seyden-Penne Reduction by the Alumino- and Borohydrides in Organic Synthesis 2nd ed. 1997 Wiley-VCH New York, NY 40
11. N.Y. Fu, X.M. Zhao, Y.F. Yuan, and J.T. Wang Chin. Chem. Lett. 14 2003 1018
12. G.L. Larson, and J.L. Fry Ionic and Organometallic-catalyzed Organosilane Reductions 2010 John Wiley & Sons Hoboken, NJ 69 84
13. L.Y. Chan, J.S.K. Lim, and S. Kim Synlett 2011 2862
14. N. Sakai, K. Nagasawa, R. Ikeda, Y. Nakaike, and T. Konakahara Tetrahedron Lett. 52 2011 3133
15. G.K.S. Prakash, C. Do, T. Mathew, and G.A. Olah Catal. Lett. 141 2011 507
16. R.J. Rahaim Jr., and R.E. Maleczka Jr. Org. Lett. 13 2011 584
17. D.R. Zuidema, S.L. Williams, K.J. Wert, K.J. Bosma, A.L. Smith, and R.C. Mebane Synth. Commun. 41 2011 2927
18. S. Ram, and L.D. Spicer Tetrahedron Lett. 29 1988 3741
19. J.T. Kuethe, K.G. Childers, Z. Peng, M. Journet, G.R. Humphrey, T. Vickery, D. Bachert, and T.T. Lam Org. Process Res. Dev. 13 2009 576
20. J.O. Saunders Sodium Hypophosphite L.A. Paquette, Encyclopedia of Reagents for Organic Chemistry vol. 7 1995 Wiley New York, NY 4587
21. V.V. Popik Hypophosphorous Acid L.A. Paquette, Encyclopedia of Reagents for Organic Chemistry vol. 4 1995 Wiley Chichester, UK 2790 2792
22. L.D. Hicks, J.K. Han, and A.J. Fry Tetrahedron Lett. 41 2000 7817
23. G.G. Wu, F.X. Chen, D. LaFrance, Z. Liu, S.G. Greene, Y.-S. Wong, and J. Xie Org. Lett. 13 2011 5220
24. J.E. Milne, T. Storz, J.T. Colyer, O.R. Thiel, M.D. Seran, R.D. Larsen, and J.A. Murry J. Org. Chem. 76 2011 9519
25. H.B. Henbest, and T.R.B. Mitchell J. Chem. Soc. C 1970 785
26. B.T. Khai, and A. Arcelli J. Org. Chem. 54 1989 949
27. B.T. Khai, and A. Arcelli Tetrahedron Lett. 37 1996 6599
28. C. Guyon, E. Métay, N. Duguet, and M. Lemaire Eur. J. Org. Chem. 2013 5439
29. V.J. Demopoulos Synth. Commun. 19 1989 2585
30. R.S. Al-awar, J.E. Ray, K.A. Hecker, J. Huang, P.P. Waid, C. Shih, H.B. Brooks, C.D. Spencer, S.A. Watkins, B.R. Patel, N.B. Stamm, C.A. Ogg, R.M. Schultz, E.L. Considine, M.M. Faul, K.A. Sullivan, S.P. Kolis, J.L. Grutsch, and S. Joseph Bioorg. Med. Chem. Lett. 14 2004 3217
31. K. Kai, J. Horita, K. Wakasa, and H. Miyagawa Phytochemistry 68 2007 1651
32. C. Villarreal, and R. Martínez Synthesis 2010 3346
33. Elder, A.; Harriman, G.; Leit, S.; Li, J.; Sard, H.; Zhang, Y.; Wilson, D. WO2011019738, 2011
34. Altmann, E.; Hommel, U.; Lorthiois, E. L. J.; Maibaum, J. K.; Ostermann, N.; Quancard, J.; Randl, S. A.; Simic, O.; Vulpetti, A.; Rogel, O. WO2012093101, 2012
35. A.F. Brigas, C.S.C. Fonseca, and R.A.W. Johnstone J. Mol. Catal. A: Chem. 246 2006 100
36. B.T. Khai, and A. Arcelli Chem. Ber. 126 1993 2265
37. S.K. Boyer, J. Bach, J. McKenna, and E. Jagdmann J. Org. Chem. 50 1985 3408
38. M. Baron, E. Métay, M. Lemaire, and F. Popowycz Green Chem. 15 2013 1006
39. J. Muzart Tetrahedron 61 2005 9423
40. S. Sawadjoon, A. Lundstedt, and J.S.M. Samec; ACS Catal. 3 2013 635
41. A. Furuta, and H. Nishiyama Tetrahedron Lett. 49 2008 110
42. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 118 1996 2521
43. C.H. Depuy, and A.L. Schultz J. Org. Chem. 39 1974 878
44. H.F. Koch, W. Tumas, and R. Knoll J. Am. Chem. Soc. 103 1981 5423
45. T. Okano, K. Ito, and T. Ueda J. Fluorine Chem. 32 1986 377
46. A.P.G. Kieboom, J.F. De Kreuk, and H. Van Bekkum J. Catal. 20 1971 58
47. Y. Motoyama, K. Kamo, and H. Nagashima Org. Lett. 11 2009 1345
48. T. Saito, Y. Nishimoto, M. Yasuda, and A. Baba J. Org. Chem. 71 2006 8516
49. T. Inagaki, L.T. Phong, A. Furuta, J.-I. Ito, and H. Nishiyama Chem. - Eur. J. 16 2010 3090
50. M.C. Breschi, V. Calderone, M. Digiacomo, M. Macchia, A. Martelli, E. Martinotti, F. Minutolo, S. Rapposelli, A. Rossello, L. Testai, and A. Balsamo J. Med. Chem. 49 2006 2628
51. S. Drouet, C.O. Paul-Roth, and G. Simonneaux Tetrahedron 65 2009 2975
52. J.W. Hilborn, E. MacKnight, J.A. Pincock, and P.J. Wedge J. Am. Chem. Soc. 116 1994 3337
53. M. Takasaki, Y. Motoyama, K. Higashi, S.-H. Yoon, I. Mochida, and H. Nagashima Org. Lett. 10 2008 1601
54. L. Huang, X. Zhang, and Y. Zhang Org. Lett. 11 2009 3730
55. K. Nemoto, H. Yoshida, N. Egusa, N. Morohashi, and T. Hattori J. Org. Chem. 75 2010 7855
56. B.-T. Guan, S.-K. Xiang, B.-Q. Wang, Z.-P. Sun, Y. Wang, K.-Q. Zhao, and Z.-J. Shi J. Am. Chem. Soc. 130 2008 3268
57. T.-P. Liu, C.-H. Xing, and Q.-S. Hu Angew. Chem., Int. Ed. 49 2010 2909
58. N. Sakai, T. Moriya, and T. Konakahara J. Org. Chem. 72 2007 5920
59. Y.-S. Feng, W. Wu, Z.-Q. Xu, Y. Li, M. Li, and H.-J. Xu Tetrahedron 68 2012 2113
60. S. Cabiddu, D. Cancellu, C. Floris, G. Gelli, and S. Melis Synthesis 1988 888
61. M.G. Banwell, B.D. Kelly, O.J. Kokas, and D.W. Lupton Org. Lett. 5 2003 2497