Biomimetic transfer hydrogenation of 2-alkoxy- and 2-aryloxyketones with iron-porphyrin catalysts

Tetrahedron

Volumn 64, Issue 17, 2008, Pages 3867-3876

  Enthaler, Stephan ^a   Spilker, Björn ^a   Erre, Giulia ^a   Junge, Kathrin ^a   Tse, Man Kin ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 HYDROXYKETONE DERIVATIVE; 2 (2 TERT BUTYL 4 METHYLPHENOXY) 1 PHENYLETHANOL; 2 (2 TERT BUTYL 4 METHYLPHENOXY)ACETOPHENONE; 2 (2,6 DI ISO PROPYLPHENOXY) 1 PHENYLETHANOL; 2 (2,6 DI ISO PROPYLPHENOXY)ACETOPHENONE; 2 (4 CHLOROPHENOXY) 1 PHENYLETHANOL; 2 (4 CHLOROPHENOXY)ACETOPHENONE; 2 (TERT BUTYLDIMETHYLSILYLOXY) 1 PHENYLETHANONE; 2 MORPHOLINO ACETOPHENONE; 2 OXO 2 PHENYLETHYL ACETATE; 2 PHENOXY 1 (4' METHOXYPHENYL)ETHANOL; 2 PHENOXY 1 (4' METHYLPHENYL)ETHANOL; 2 PHENOXY 1 PHENYLETHANOL; 2 PHENOXY 2,3 DIHYDRO 1H INDEN 1 OL; 2 PHENOXY 2,3 DIHYDRO 1H INDEN 1 ONE; 2 PHENOXY 4' METHOXYACETOPHENONE; 2 PHENOXY 4' METHYLACETOPHENONE; 2 PHENOXY ACETOPHENONE; 2 PROPANOL; 3,3 DIMETHYL 1 PHENOXYBUTAN 2 OL; 3,3 DIMETHYL 1 PHENOXYBUTAN 2 ONE; IRON; KETONE DERIVATIVE; PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CATALYST; CHEMICAL STRUCTURE; HYDROGENATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 40649083478     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.083     Document Type: Article

References (58)

1. (a) R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 Wiley New York, NY
2. (b) B. Cornils W.A. Herrmann Applied Homogeneous Catalysis with Organometallic Compounds 1996 Wiley-VCH Weinheim
3. (c) E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Berlin
4. (d) M. Kitamura R. Noyori S.-I. Murahashi Ruthenium in Organic Synthesis 2004 Wiley-VCH Weinheim
5. (e) M. Beller C. Bolm Transition Metals for Organic Synthesis 2nd ed. 2004 Wiley-VCH Weinheim
6. (f) J.-E. Bäckvall Modern Oxidation Methods 2004 Wiley-VCH Weinheim
7. (a) G. Zassinovich G. Mestroni S. Gladiali Chem. Rev. 51 1992 1051 1069
8. (b) R. Noyori S. Hashiguchi Acc. Chem. Res. 30 1997 97 102
9. (c) S. Gladiali G. Mestroni M. Beller C. Bolm Transition Metals for Organic Synthesis 2nd ed. 2004 Wiley-VCH Weinheim 145 166
10. (d) H.-U. Blaser C. Malan B. Pugin F. Spindler M. Studer Adv. Synth. Catal. 345 2003 103 151
11. (e) S. Gladiali E. Alberico Chem. Soc. Rev. 35 2006 226 236
12. (f) J.S.M. Samec J.-E. Bäckvall P.G. Andersson P. Brandt Chem. Soc. Rev. 35 2006 237 248
13. Selected recent examples of transfer hydrogenations:
14. (a) A. Schlatter M.K. Kundu W.-D. Woggon Angew. Chem., Int. Ed. 43 2004 6731 6734
15. (b) D. Xue Y.-C. Chen X. Cui Q.-W. Wang J. Zhu J.-G. Deng J. Org. Chem. 70 2005 3584 3591
16. (c) X. Wu X. Li F. King J. Xiao Angew. Chem., Int. Ed. 44 2005 3407 3411
17. (d) A.M. Hayes D.J. Morris G.J. Clarkson M. Wills J. Am. Chem. Soc. 127 2005 7318 7319
18. (e) W. Baratta G. Chelucci S. Gladiali K. Siega M. Toniutti M. Zanette E. Zangrando P. Rigo Angew. Chem., Int. Ed. 44 2005 6214 6219
19. (f) S. Enthaler R. Jackstell B. Hagemann K. Junge G. Erre M. Beller J. Organomet. Chem. 691 2006 4652 4659
20. (g) S. Enthaler B. Hagemann S. Bhor G. Anilkumar M.K. Tse B. Bitterlich K. Junge G. Erre M. Beller Adv. Synth. Catal. 349 2007 853 860
21. (a) F.K. Cheung A.M. Hayes J. Hannedouche A.S.Y. Yim M. Wills J. Org. Chem. 70 2005 3188 3197
22. (b) D.S. Matharu D.J. Morris A.M. Kawamoto G.J. Clarkson M. Wills Org. Lett. 7 2005 5489 5491
23. (c) P. Peach D.J. Cross J.A. Kenny I. Mann I. Houson L. Campbell T. Walsgrove M. Wills Tetrahedron 62 2006 1864 1876
24. (d) T. Hamada T. Torii K. Izawa T. Ikariya Tetrahedron 60 2004 7411 7417
25. C. Bolm J. Legros J. Le Paih L. Zani Chem. Rev. 104 2004 6217 6254
26. R. Noyori I. Umeda T. Ishigami J. Org. Chem. 37 1972 1542 1545
27. (a) K. Jothimony S. Vancheesan J. Mol. Catal. 52 1989 301 304
28. (b) K. Jothimony S. Vancheesan J.C. Kuriacose J. Mol. Catal. 32 1985 11 16
29. C. Bianchini E. Farnetti M. Graziani M. Peruzzini A. Polo Organometallics 12 1993 3753 3761
30. J.-S. Chen L.-L. Chen Y. Xing G. Chen W.-Y. Shen Z.-R. Dong Y.-Y. Li J.-X. Gao Huaxue Xuebao 62 2004 1745 1750
31. C. Siu-Seng F. Freutel A.J. Lough R.H. Morris Angew. Chem. Int. Ed. 47 2008 940 943
32. See also for iron-catalyzed hydrogenation:
33. (a) C.P. Casey H. Guan J. Am. Chem. Soc. 129 2007 5816 5817
34. (b) M. Bullock Angew. Chem. 119 2007 7504 7507
35. (c) S.C. Bart E. Lobkovsky P.J. Chirik J. Am. Chem. Soc. 126 2004 13794 13807
36. (d) A.M. Archer M.W. Bouwkamp M.-P. Cortez E. Lobkovsky P.J. Chirik Organometallics 25 2006 4269 4278
37. (e) R.J. Trovitch E. Lobkovsky P.J. Chirik Inorg. Chem. 45 2006 7252 7260
38. (f) S.C. Bart E.J. Hawrelak E. Lobkovsky P.J. Chirik Organometallics 24 2005 5518 5527
39. For iron-catalyzed hydrosilylation:
40. (g) H. Nishiyama A. Furuta Chem. Commun. 7 2007 760 762
41. (h) N.S. Shaikh K. Junge M. Beller Org. Lett. 9 2007 5429 5432
42. (i) Shaikh, N. S.; Enthaler, S.; Junge, K.; Beller, M. Angew. Chem. , in press.
43. (a) S. Enthaler B. Hagemann G. Erre K. Junge M. Beller Chem. Asian J. 1 2006 598 604
44. (b) S. Enthaler G. Erre M.K. Tse K. Junge M. Beller Tetrahedron Lett. 47 2006 8095 8099
45. H. Adkins R.M. Elofson A.G. Rossow C.C. Robinson J. Am. Chem. Soc. 71 1949 3622 3629
46. (a) C.-L. Sun R.-F. Pang H. Zhang M. Yang Bioorg. Med. Chem. Lett. 15 2005 3257 3262
47. (b) C. Fabbri M. Bietti O. Lanzalunga J. Org. Chem. 70 2005 2720 2728
48. (c) P.H. Kandanarachchi T. Autrey J.A. Franz J. Org. Chem. 67 2002 7937 7945
49. K.M. Kadish O.S. Finikova E. Espinosa C.P. Gros G. De Stefano A.V. Cheprakov I.P. Beletskaya R. Guilard J. Porphyrins Phthalocyanines 8 2004 1062 1066
50. C. Alexiou A.B.P. Lever Coord. Chem. Rev. 216–217 2001 45 54
51. J.A. Hodge M.G. Hill H.B. Gray Inorg. Chem. 34 1995 809 812
52. (a) C. Hu B.C. Noll C.E. Schulz W.R. Scheidt Inorg. Chem. 46 2007 619 621
53. (b) F. Melin S. Choua M. Bernard P. Turek J. Weiss Inorg. Chem. 45 2006 10750 10757
54. (c) C. Liu D.-M. Shen Q.-Y. Chen Eur. J. Org. Chem. 12 2006 2703 2706
55. (d) C. Ruzie P. Even D. Ricard T. Roisnel B. Boitrel Inorg. Chem. 45 2006 1338 1348
56. (e) P. Even C. Ruzie D. Ricard B. Boitrel Org. Lett. 7 2005 4325 4328
57. (a) J.S. Lindsey H.C. Hsu I.C. Schreiman Tetrahedron Lett. 27 1986 4969 4970
58. (b) J.S. Lindsey I.C. Schreiman H.C. Hsu P.C. Kearney A.M. Marguerettaz J. Org. Chem. 52 1987 827 836