SCOPUS 정보 검색 플랫폼 - 논문 보기

메뉴 건너뛰기

Chemical Science

Volumn 3, Issue 3, 2012, Pages 887-891

Direct aerobic α,β-dehydrogenation of aldehydes and ketones with a Pd(TFA) 2/4,5-diazafluorenone catalyst

(3) Diao, Tianning a Wadzinski, Tyler J a Stahl, Shannon S a

a UNIVERSITY OF WISCONSIN MADISON (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC KETONES; C-H BOND; CATALYST SYSTEM; CATALYTIC MECHANISMS; CYCLOPENTANONE; DEHYDROGENATION CATALYSTS; MECHANISTIC STUDIES; STEPWISE METHODS;

ALDEHYDES; CATALYSTS; DEHYDROGENATION; KETONES;

ORGANIC COMPOUNDS;

EID: 84857338165 PISSN: 20416520 EISSN: 20416539 Source Type: Journal
DOI: 10.1039/c1sc00724f Document Type: Article

Times cited : (150)

References (48)

1
- 0003417469
- in, ed. B. M. Trost and I. Fleming, Elsevier, Oxford, 7, p. 119
- D. R. Buckle and I. L. Pinto, in Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Fleming, Elsevier, Oxford, 1991, vol. 7, p. 119
- (1991) Comprehensive Organic Synthesis
- Buckle, D.R.¹ Pinto, I.L.²

2
- 0003543593
- in, John Wiley & Sons, New York, p. 251
- R. C. Larock, in Comprehensive Organic Transformations, John Wiley & Sons, New York, 1999, p. 251
- (1999) Comprehensive Organic Transformations
- Larock, R.C.¹

3
- 0001270910
- B. Miller H. Wong Tetrahedron 1972 28 2369
- (1972) Tetrahedron , vol.28 , pp. 2369
- Miller, B.¹ Wong, H.²

4
- 0000326796
- For a leading reference and review of selenium based reagents, see
- P. L. Stotter K. A. Hill J. Org. Chem. 1973 38 2576
- (1973) J. Org. Chem. , vol.38 , pp. 2576
- Stotter, P.L.¹ Hill, K.A.²

5
- 33947085849
- K. B. Sharpless R. F. Lauer A. Y. Teranishi J. Am. Chem. Soc. 1973 95 6137
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 6137
- Sharpless, K.B.¹ Lauer, R.F.² Teranishi, A.Y.³

6
- 0002389988
- Related sulfoxide elimination reactions are also used. For a leading reference, see
- H. J. Reich Acc. Chem. Res. 1979 12 22
- (1979) Acc. Chem. Res. , vol.12 , pp. 22
- Reich, H.J.¹

7
- 33847799030
- II, but catalytic examples have also been reported. See the following leading references
- B. M. Trost T. N. Salzmann K. Hiroi J. Am. Chem. Soc. 1976 98 4887
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 4887
- Trost, B.M.¹ Salzmann, T.N.² Hiroi, K.³

8
- 33746494993
- Y. Ito T. Hirao T. Saegusa J. Org. Chem. 1978 43 1011
- (1978) J. Org. Chem. , vol.43 , pp. 1011
- Ito, Y.¹ Hirao, T.² Saegusa, T.³

9
- 0028899917
- R. C. Larock T. R. Hightower G. A. Kraus P. Hahn D. Zheng Tetrahedron Lett. 1995 36 2423
- (1995) Tetrahedron Lett. , vol.36 , pp. 2423
- Larock, R.C.¹ Hightower, T.R.² Kraus, G.A.³ Hahn, P.⁴ Zheng, D.⁵

10
- 17444428665
- J.-Q. Yu H.-C. Wu E. J. Corey Org. Lett. 2005 7 1415
- (2005) Org. Lett. , vol.7 , pp. 1415
- Yu, J.-Q.¹ Wu, H.-C.² Corey, E.J.³

11
- 0014072079
- D. Walker J. D. Hiebert Chem. Rev. 1967 67 153
- (1967) Chem. Rev. , vol.67 , pp. 153
- Walker, D.¹ Hiebert, J.D.²

12
- 84907686893
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- in, John Wiley & Sons, Inc., New York
- D. R. Buckle, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Inc., New York, 2010
- (2010) Encyclopedia of Reagents for Organic Synthesis
- Buckle, D.R.¹

13
- 0034625897
- K. C. Nicolaou Y.-L. Zhong P. S. Baran J. Am. Chem. Soc. 2000 122 7596
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 7596
- Nicolaou, K.C.¹ Zhong, Y.-L.² Baran, P.S.³

14
- 0037070535
- K. C. Nicolaou T. Montagnon P. S. Baran Y.-L. Zhong J. Am. Chem. Soc. 2002 124 2245
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 2245
- Nicolaou, K.C.¹ Montagnon, T.² Baran, P.S.³ Zhong, Y.-L.⁴

15
- 0037087704
- K. C. Nicolaou T. Montagnon P. S. Baran Angew. Chem., Int. Ed. 2002 41 993
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 993
- Nicolaou, K.C.¹ Montagnon, T.² Baran, P.S.³

16
- 0037087571
- For a method employing catalytic 2-iodoxybenzene sulfonate (IBS) in combination with stoichiometric Oxone®, see
- K. C. Nicolaou D. L. F. Gray T. Montagnon S. T. Harrison Angew. Chem., Int. Ed. 2002 41 996
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 996
- Nicolaou, K.C.¹ Gray, D.L.F.² Montagnon, T.³ Harrison, S.T.⁴

17
- 67749120518
- For a recent review of efforts toward this goal, see
- M. Uyanik M. Akakura K. Ishihara J. Am. Chem. Soc. 2009 131 251
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 251
- Uyanik, M.¹ Akakura, M.² Ishihara, K.³

18
- 77954248100
- For recent advances in Pd-catalyzed aerobic oxidation reactions, see the following references
- J. Muzart Eur. J. Org. Chem. 2010 3779
- (2010) Eur. J. Org. Chem. , pp. 3779
- Muzart, J.¹

19
- 4143153074
- S. S. Stahl Angew. Chem., Int. Ed. 2004 43 3400
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3400
- Stahl, S.S.¹

20
- 67650602181
- K. M. Gligorich M. S. Sigman Chem. Commun. 2009 3854
- (2009) Chem. Commun. , pp. 3854
- Gligorich, K.M.¹ Sigman, M.S.²

21
- 67649488045
- For leading references, see ref. 9 and the following
- X. Chen K. M. Engle D.-H. Wang J.-Q. Yu Angew. Chem., Int. Ed. 2009 48 5094
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5094
- Chen, X.¹ Engle, K.M.² Wang, D.-H.³ Yu, J.-Q.⁴

22
- 33947291370
- R. J. Theissen J. Org. Chem. 1971 36 752
- (1971) J. Org. Chem. , vol.36 , pp. 752
- Theissen, R.J.¹

23
- 0037632714
- J. Muzart J. P. Pete J. Mol. Catal. 1982 15 373
- (1982) J. Mol. Catal. , vol.15 , pp. 373
- Muzart, J.¹ Pete, J.P.²

24
- 37049084540
- T. T. Wenzel J. Chem. Soc., Chem. Commun. 1989 932
- (1989) J. Chem. Soc., Chem. Commun. , pp. 932
- Wenzel, T.T.¹

25
- 1542572820
- Y. W. Park H. H. Oh Bull. Korean Chem. Soc. 1997 18 1123
- (1997) Bull. Korean Chem. Soc. , vol.18 , pp. 1123
- Park, Y.W.¹ Oh, H.H.²

26
- 34548284970
- M. Tokunaga S. Harada T. Iwasawa Y. Obora Y. Tsuji Tetrahedron Lett. 2007 48 6860
- (2007) Tetrahedron Lett. , vol.48 , pp. 6860
- Tokunaga, M.¹ Harada, S.² Iwasawa, T.³ Obora, Y.⁴ Tsuji, Y.⁵

27
- 80052802032
- T. Diao S. S. Stahl J. Am. Chem. Soc. 2011 133 14566
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 14566
- Diao, T.¹ Stahl, S.S.²

28
- 79960078229
- Y. Izawa D. Pun S. S. Stahl Science 2011 333 209
- (2011) Science , vol.333 , pp. 209
- Izawa, Y.¹ Pun, D.² Stahl, S.S.³

29
- 84857252190
- S. M. Massey, J. A. Monn and M. J. Valli, Eur. Patent 878463, 1998
- (1998) Eur. Patent 878463
- Massey, S.M.¹ Monn, J.A.² Valli, M.J.³

30
- 34047119071
- For progress in the development of a safe and scalable flow process for aerobic oxidation, see
- F. Zhang E. D. Moher T. Y. Zhang Tetrahedron Lett. 2007 48 3277
- (2007) Tetrahedron Lett. , vol.48 , pp. 3277
- Zhang, F.¹ Moher, E.D.² Zhang, T.Y.³

31
- 77954602413
- X. Ye M. D. Johnson T. Diao M. H. Yates S. S. Stahl Green Chem. 2010 12 1180
- (2010) Green Chem. , vol.12 , pp. 1180
- Ye, X.¹ Johnson, M.D.² Diao, T.³ Yates, M.H.⁴ Stahl, S.S.⁵

32
- 67549134370
- J. Zhu J. Liu Q. Ma H. Xie J. Li H. Jiang W. Wang Adv. Synth. Catal. 2009 351 1229
- (2009) Adv. Synth. Catal. , vol.351 , pp. 1229
- Zhu, J.¹ Liu, J.² Ma, Q.³ Xie, H.⁴ Li, J.⁵ Jiang, H.⁶ Wang, W.⁷

33
- 73649125827
- J. Liu J. Zhu H. Jiang W. Wang J. Li Chem.-Asian J. 2009 4 1712
- (2009) Chem.-Asian J. , vol.4 , pp. 1712
- Liu, J.¹ Zhu, J.² Jiang, H.³ Wang, W.⁴ Li, J.⁵

34
- 78049392925
- A. N. Campbell P. B. White I. A. Guzei S. S. Stahl J. Am. Chem. Soc. 2010 132 15116
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15116
- Campbell, A.N.¹ White, P.B.² Guzei, I.A.³ Stahl, S.S.⁴

35
- 80052527468
- a values relevant to the present study, see
- A. N. Campbell E. B. Meyer S. S. Stahl Chem. Commun. 2011 47 10257
- (2011) Chem. Commun. , vol.47 , pp. 10257
- Campbell, A.N.¹ Meyer, E.B.² Stahl, S.S.³

36
- 6444232702
- W. S. Matthews J. E. Bares J. E. Bartmess F. G. Bordwell F. J. Cornforth G. E. Drucker Z. Margolin R. J. McCallum G. J. McCollum N. R. Vanier J. Am. Chem. Soc. 1975 97 7006
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 7006
- Matthews, W.S.¹ Bares, J.E.² Bartmess, J.E.³ Bordwell, F.G.⁴ Cornforth, F.J.⁵ Drucker, G.E.⁶ Margolin, Z.⁷ McCallum, R.J.⁸ McCollum, G.J.⁹ Vanier, N.R.¹⁰

37
- 0001421515
- F. G. Bordwell J. E. Bares J. E. Bartmess G. E. Drucker J. Gerhold G. J. McCollum M. Van Der Puy N. R. Vanier W. S. Matthews J. Org. Chem. 1977 42 326
- (1977) J. Org. Chem. , vol.42 , pp. 326
- Bordwell, F.G.¹ Bares, J.E.² Bartmess, J.E.³ Drucker, G.E.⁴ Gerhold, J.⁵ McCollum, G.J.⁶ Van Der Puy, M.⁷ Vanier, N.R.⁸ Matthews, W.S.⁹

38
- 0001743486
- F. G. Bordwell J. A. Harrelson Jr. Can. J. Chem. 1990 68 1714
- (1990) Can. J. Chem. , vol.68 , pp. 1714
- Bordwell, F.G.¹ Harrelson Jr., J.A.²

39
- 84857295125
- a values, see
- a values, see: http://www.chem.wisc.edu/areas/reich/pkatable/

40
- 34248226610
- D. Patel S. Shukla S. Gupta Int. J. Oncol. 2007 30 233
- (2007) Int. J. Oncol. , vol.30 , pp. 233
- Patel, D.¹ Shukla, S.² Gupta, S.³

41
- 13244291574
- B. M. Choudary K. V. S. Ranganath J. Yadav M. Lakshmi Kantam Tetrahedron Lett. 2005 46 1369
- (2005) Tetrahedron Lett. , vol.46 , pp. 1369
- Choudary, B.M.¹ Ranganath, K.V.S.² Yadav, J.³ Lakshmi Kantam, M.⁴

42
- 0035793664
- T. Kondo K. Oyama K. Yoshida Angew. Chem., Int. Ed. 2001 40 894
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 894
- Kondo, T.¹ Oyama, K.² Yoshida, K.³

43
- 61449170185
- D. Si Y. Wang Y. Zhou Y. Guo J. Wang H. Zhou Z. Li J. P. Fawcett Drug Metab. Dispos. 2009 37 629
- (2009) Drug Metab. Dispos. , vol.37 , pp. 629
- Si, D.¹ Wang, Y.² Zhou, Y.³ Guo, Y.⁴ Wang, J.⁵ Zhou, H.⁶ Li, Z.⁷ Fawcett, J.P.⁸

44
- 33749444911
- II-H intermediate, has been isolated from a "Saegusa"-type oxidation reaction
- R. Cermak S. Wolffram Curr. Drug Metab. 2006 7 729
- (2006) Curr. Drug Metab. , vol.7 , pp. 729
- Cermak, R.¹ Wolffram, S.²

45
- 0033549545
- 0, as shown in Scheme 1. See
- S. Porth J. W. Bats D. Trauner G. Giester J. Mulzer Angew. Chem., Int. Ed. 1999 38 2015
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2015
- Porth, S.¹ Bats, J.W.² Trauner, D.³ Giester, G.⁴ Mulzer, J.⁵

46
- 42649133825
- M. M. Konnick S. S. Stahl J. Am. Chem. Soc. 2008 130 5753
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 5753
- Konnick, M.M.¹ Stahl, S.S.²

47
- 62349094304
- B. V. Popp S. S. Stahl Chem.-Eur. J. 2009 15 2915
- (2009) Chem.-Eur. J. , vol.15 , pp. 2915
- Popp, B.V.¹ Stahl, S.S.²

48
- 80052078778
- N. Decharin B. V. Popp S. S. Stahl J. Am. Chem. Soc. 2011 133 13268
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 13268
- Decharin, N.¹ Popp, B.V.² Stahl, S.S.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.