SCOPUS 정보 검색 플랫폼

RSC Advances

Volumn 5, Issue 56, 2015, Pages 44928-44932

Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis

(4) Dinda, Milan a Bose, Chandan b Ghosh, Tridev a Maity, Soumitra a,b

a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE (India)

b INDIAN SCHOOL OF MINES (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ESTERIFICATION; ESTERS; INCANDESCENT LAMPS; LIGHT EMITTING DIODES;

BUILDING BLOCKES; CROSS DEHYDROGENATIVE COUPLINGS; ESTER DERIVATIVES; PHOTO-INDUCED; PHOTOREDOX CATALYSIS; ROOM TEMPERATURE; SYNTHETIC INTERMEDIATES; VISIBLE LIGHT;

LIGHT;

EID: 84930193198 PISSN: None EISSN: 20462069 Source Type: Journal
DOI: 10.1039/c5ra05719a Document Type: Article

Times cited : (41)

References (73)

1
- 33846979420
- N. S. Lewis Science 2007 315 798
- (2007) Science , vol.315 , pp. 798
- Lewis, N.S.¹

2
- 34250862807
- D. J. C. Constable P. J. Dunn J. D. Hayler G. R. Humphrey J. L. Leazer R. J. Linderman K. Lorenz J. Manley B. A. Pearlman A. Wells A. Zaks T. Y. Zhang Green Chem. 2007 9 411
- (2007) Green Chem. , vol.9 , pp. 411
- Constable, D.J.C.¹ Dunn, P.J.² Hayler, J.D.³ Humphrey, G.R.⁴ Leazer, J.L.⁵ Linderman, R.J.⁶ Lorenz, K.⁷ Manley, J.⁸ Pearlman, B.A.⁹ Wells, A.¹⁰ Zaks, A.¹¹ Zhang, T.Y.¹²

3
- 1442326812
- For recent reviews on CDC, see
- A. Albini M. Fagnoni Green Chem. 2004 6 1
- (2004) Green Chem. , vol.6 , pp. 1
- Albini, A.¹ Fagnoni, M.²

4
- 79952678116
- C. S. Yeung V. M. Dong Chem. Rev. 2011 111 1215
- (2011) Chem. Rev. , vol.111 , pp. 1215
- Yeung, C.S.¹ Dong, V.M.²

5
- 79151486176
- M. Klussmann D. Sureshkumar Synthesis 2011 353
- (2011) Synthesis , pp. 353
- Klussmann, M.¹ Sureshkumar, D.²

6
- 79961232246
- X. Bugaut F. Glorius Angew. Chem., Int. Ed. 2011 50 7479
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 7479
- Bugaut, X.¹ Glorius, F.²

7
- 80054728269
- S. H. Cho J. Y. Kim J. Kwak S. Chang Chem. Soc. Rev. 2011 40 5068
- (2011) Chem. Soc. Rev. , vol.40 , pp. 5068
- Cho, S.H.¹ Kim, J.Y.² Kwak, J.³ Chang, S.⁴

8
- 75749099888
- J. A. Ashenhurst Chem. Soc. Rev. 2010 39 540
- (2010) Chem. Soc. Rev. , vol.39 , pp. 540
- Ashenhurst, J.A.¹

9
- 77749292887
- C. J. Scheuermann Chem.-Asian J. 2010 5 436
- (2010) Chem.-Asian J. , vol.5 , pp. 436
- Scheuermann, C.J.¹

10
- 79151478024
- W. J. Yoo C.-J. Li Top. Curr. Chem. 2010 292 281
- (2010) Top. Curr. Chem. , vol.292 , pp. 281
- Yoo, W.J.¹ Li, C.-J.²

11
- 84930237498
- For the ideal chemical synthesis, see
- C.-J. Li Acc. Chem. Res. 2009 42 3352
- (2009) Acc. Chem. Res. , vol.42 , pp. 3352
- Li, C.-J.¹

12
- 84926433821
- S. Balieu G. E. Hallett M. Burns T. Bootwicha J. Studley V. K. Aggarwal J. Am. Chem. Soc. 2015 137 4398
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 4398
- Balieu, S.¹ Hallett, G.E.² Burns, M.³ Bootwicha, T.⁴ Studley, J.⁵ Aggarwal, V.K.⁶

13
- 77954562085
- T. Gaich P. S. Baran J. Org. Chem. 2010 75 4657
- (2010) J. Org. Chem. , vol.75 , pp. 4657
- Gaich, T.¹ Baran, P.S.²

14
- 70350500463
- T. Newhouse P. S. Baran R. W. Hoffmann Chem. Soc. Rev. 2009 38 3010
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3010
- Newhouse, T.¹ Baran, P.S.² Hoffmann, R.W.³

15
- 0004938188
- For recent examples on C-P bond formation by CDC, see
- J. B. Hendrickson J. Am. Chem. Soc. 1975 97 5784
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 5784
- Hendrickson, J.B.¹

16
- 84878147014
- W.-B. Sun Y.-F. Ji X.-Q. Pan S.-F. Zhou J.-P. Zou W. Zhang O. Asekun Synthesis 2013 45 1529
- (2013) Synthesis , vol.45 , pp. 1529
- Sun, W.-B.¹ Ji, Y.-F.² Pan, X.-Q.³ Zhou, S.-F.⁴ Zou, J.-P.⁵ Zhang, W.⁶ Asekun, O.⁷

17
- 84860383313
- C. Hou Y. Ren R. Lang X. Hu C. Xia F. Li Chem. Commun. 2012 48 5181
- (2012) Chem. Commun. , vol.48 , pp. 5181
- Hou, C.¹ Ren, Y.² Lang, R.³ Hu, X.⁴ Xia, C.⁵ Li, F.⁶

18
- 84862579207
- J. Xie H. Li Q. Xue Y. Cheng C. Zhu Adv. Synth. Catal. 2012 354 1646
- (2012) Adv. Synth. Catal. , vol.354 , pp. 1646
- Xie, J.¹ Li, H.² Xue, Q.³ Cheng, Y.⁴ Zhu, C.⁵

19
- 77249094730
- X.-Q. Pan J.-P. Zou G.-L. Zhang W. Zhang Chem. Commun. 2010 46 1721
- (2010) Chem. Commun. , vol.46 , pp. 1721
- Pan, X.-Q.¹ Zou, J.-P.² Zhang, G.-L.³ Zhang, W.⁴

20
- 84855447048
- H. Wang X. Li F. Wua B. Wan Tetrahedron Lett. 2012 53 681
- (2012) Tetrahedron Lett. , vol.53 , pp. 681
- Wang, H.¹ Li, X.² Wua, F.³ Wan, B.⁴

21
- 84857232180
- For recent examples on C-N bond formation by CDC, see
- K. Alagiri P. Devadig K. R. Prabhu Tetrahedron Lett. 2012 53 1456
- (2012) Tetrahedron Lett. , vol.53 , pp. 1456
- Alagiri, K.¹ Devadig, P.² Prabhu, K.R.³

22
- 84863619824
- C. Zhang X. Zong L. Zhang N. Jiao Org. Lett. 2012 14 3280
- (2012) Org. Lett. , vol.14 , pp. 3280
- Zhang, C.¹ Zong, X.² Zhang, L.³ Jiao, N.⁴

23
- 84862665080
- R. T. Gephart III D. L. Huang M. J. B. Aguila G. Schmidt A. Shahu T. H. Warren Angew. Chem., Int. Ed. 2012 51 6488
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 6488
- Gephart, R.T.¹ Huang, D.L.² Aguila, M.J.B.³ Schmidt, G.⁴ Shahu, A.⁵ Warren, T.H.⁶

24
- 80052714613
- Q. Xia W. Chen H. Qiu J. Org. Chem. 2011 76 7577
- (2011) J. Org. Chem. , vol.76 , pp. 7577
- Xia, Q.¹ Chen, W.² Qiu, H.³

25
- 84868363747
- R. Samanta J. O. Bauer C. Strohmann A. P. Antonchick Org. Lett. 2012 14 5518
- (2012) Org. Lett. , vol.14 , pp. 5518
- Samanta, R.¹ Bauer, J.O.² Strohmann, C.³ Antonchick, A.P.⁴

26
- 84855681825
- F.-T. Du J.-X. Ji Chem. Sci. 2012 3 460
- (2012) Chem. Sci. , vol.3 , pp. 460
- Du, F.-T.¹ Ji, J.-X.²

27
- 79960198973
- T. Froehr C. P. Sindlinger U. Kloeckner P. Finkbeiner B. J. Nachtsheim Org. Lett. 2011 13 3754
- (2011) Org. Lett. , vol.13 , pp. 3754
- Froehr, T.¹ Sindlinger, C.P.² Kloeckner, U.³ Finkbeiner, P.⁴ Nachtsheim, B.J.⁵

28
- 84863012389
- J. Yu S.-S. Liu J. Cui X.-S. Hou C. Zhang Org. Lett. 2012 14 832
- (2012) Org. Lett. , vol.14 , pp. 832
- Yu, J.¹ Liu, S.-S.² Cui, J.³ Hou, X.-S.⁴ Zhang, C.⁵

29
- 81255190874
- C. Zhang Z. Xu L. Zhang N. Jiao Angew. Chem., Int. Ed. 2011 50 11088
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 11088
- Zhang, C.¹ Xu, Z.² Zhang, L.³ Jiao, N.⁴

30
- 78650279320
- For recent examples on C-O bond formation by CDC, see
- J. Y. Kim S. H. Cho J. Joseph S. Chang Angew. Chem., Int. Ed. 2010 49 9899
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 9899
- Kim, J.Y.¹ Cho, S.H.² Joseph, J.³ Chang, S.⁴

31
- 84903817630
- I. B. Krylov A. O. Terent'ev V. P. Timofeev B. N. Shelimov R. A. Novikov V. M. Merkulova G. I. Nikishin Adv. Synth. Catal. 2014 356 2266
- (2014) Adv. Synth. Catal. , vol.356 , pp. 2266
- Krylov, I.B.¹ Terent'Ev, A.O.² Timofeev, V.P.³ Shelimov, B.N.⁴ Novikov, R.A.⁵ Merkulova, V.M.⁶ Nikishin, G.I.⁷

32
- 84884500418
- A. O. Terent'ev I. B. Krylov V. P. Timofeev Z. A. Starikova V. M. Merkulova A. I. Ilovaisky G. I. Nikishin Adv. Synth. Catal. 2013 355 2375
- (2013) Adv. Synth. Catal. , vol.355 , pp. 2375
- Terent'Ev, A.O.¹ Krylov, I.B.² Timofeev, V.P.³ Starikova, Z.A.⁴ Merkulova, V.M.⁵ Ilovaisky, A.I.⁶ Nikishin, G.I.⁷

33
- 84864623519
- S. K. Rout S. Guin K. K. Ghara A. Banerjee B. K. Patel Org. Lett. 2012 14 3982
- (2012) Org. Lett. , vol.14 , pp. 3982
- Rout, S.K.¹ Guin, S.² Ghara, K.K.³ Banerjee, A.⁴ Patel, B.K.⁵

34
- 84865795296
- D. Srimani E. Balaraman B. Gnanaprakasam Y. Ben-David D. Milstein Adv. Synth. Catal. 2012 354 2403
- (2012) Adv. Synth. Catal. , vol.354 , pp. 2403
- Srimani, D.¹ Balaraman, E.² Gnanaprakasam, B.³ Ben-David, Y.⁴ Milstein, D.⁵

35
- 84863618421
- E. Shi Y. Shao S. Chen H. Hu Z. Liu J. Zhang X. Wan Org. Lett. 2012 14 3384
- (2012) Org. Lett. , vol.14 , pp. 3384
- Shi, E.¹ Shao, Y.² Chen, S.³ Hu, H.⁴ Liu, Z.⁵ Zhang, J.⁶ Wan, X.⁷

36
- 84869417063
- M. Baidya K. A. Griffin H. Yamamoto J. Am. Chem. Soc. 2012 134 18566
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 18566
- Baidya, M.¹ Griffin, K.A.² Yamamoto, H.³

37
- 79957455919
- M. Uyanik D. Suzuki T. Yasui K. Ishihara Angew. Chem., Int. Ed. 2011 50 5331
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 5331
- Uyanik, M.¹ Suzuki, D.² Yasui, T.³ Ishihara, K.⁴

38
- 82455192747
- G. S. Kumar C. U. Maheswari R. A. Kumar M. L. Kantam K. R. Reddy Angew. Chem., Int. Ed. 2011 50 11748
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 11748
- Kumar, G.S.¹ Maheswari, C.U.² Kumar, R.A.³ Kantam, M.L.⁴ Reddy, K.R.⁵

39
- 1242280737
- Wiley-VCH, Weinheim, Germany
- J. Otera, Esterification Methods, Reactions, and Applications, Wiley-VCH, Weinheim, Germany, 2003
- (2003) Esterification Methods, Reactions, and Applications
- Otera, J.¹

40
- 84925790434
- M. Tsakos E. S. Schaffert L. L. Clement N. L. Villadsen T. B. Poulsen Nat. Prod. Rep. 2015 32 605
- (2015) Nat. Prod. Rep. , vol.32 , pp. 605
- Tsakos, M.¹ Schaffert, E.S.² Clement, L.L.³ Villadsen, N.L.⁴ Poulsen, T.B.⁵

41
- 84891569651
- Wiley-VCH, Weinheim, Germany
- J. Otera and J. Nishikido, Esterification: Methods, Reactions, and Applications, Wiley-VCH, Weinheim, Germany, 2010
- (2010) Esterification: Methods, Reactions, and Applications
- Otera, J.¹ Nishikido, J.²

42
- 74549155702
- M. Kim K. J. Han Synth. Commun. 2009 39 4467
- (2009) Synth. Commun. , vol.39 , pp. 4467
- Kim, M.¹ Han, K.J.²

43
- 0032473802
- P. Pçchlauer W. Hendel Tetrahedron 1998 54 3489
- (1998) Tetrahedron , vol.54 , pp. 3489
- Pçchlauer, P.¹ Hendel, W.²

44
- 37049097492
- S. Kim Y. K. Ko J. Chem. Soc., Chem. Commun. 1985 473
- (1985) J. Chem. Soc., Chem. Commun. , pp. 473
- Kim, S.¹ Ko, Y.K.²

45
- 0000884928
- H. Ogura T. Kobayashi K. Shimizu K. Kawabe K. Takeda Tetrahedron Lett. 1979 20 4745
- (1979) Tetrahedron Lett. , vol.20 , pp. 4745
- Ogura, H.¹ Kobayashi, T.² Shimizu, K.³ Kawabe, K.⁴ Takeda, K.⁵

46
- 84870615882
- B. Tan N. Toda C. F. Barbaras III Angew. Chem., Int. Ed. 2012 51 12538
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 12538
- Tan, B.¹ Toda, N.² Barbaras, C.F.³

47
- 84887682913
- M. Pilo A. Porcheddu L. D. Luca Org. Biomol. Chem. 2013 11 8241
- (2013) Org. Biomol. Chem. , vol.11 , pp. 8241
- Pilo, M.¹ Porcheddu, A.² Luca, L.D.³

48
- 84862567450
- H. Yao K. Yamamoto Chem.-Asian J. 2012 7 1542
- (2012) Chem.-Asian J. , vol.7 , pp. 1542
- Yao, H.¹ Yamamoto, K.²

49
- 84865198723
- For recent reviews on photoredox catalysis, see
- H. Yao Y. Tung K. Yamamoto Tetrahedron Lett. 2012 53 5094
- (2012) Tetrahedron Lett. , vol.53 , pp. 5094
- Yao, H.¹ Tung, Y.² Yamamoto, K.³

50
- 84899868476
- M. Majek F. Filace J. A. Von Wangelin Beilstein J. Org. Chem. 2014 10 981
- (2014) Beilstein J. Org. Chem. , vol.10 , pp. 981
- Majek, M.¹ Filace, F.² Von Wangelin, J.A.³

51
- 84901756087
- D. P. Hari B. Konig Chem. Commun. 2014 50 6688
- (2014) Chem. Commun. , vol.50 , pp. 6688
- Hari, D.P.¹ Konig, B.²

52
- 84880124916
- C. K. Prier D. A. Rankic D. W. C. MacMillan Chem. Rev. 2013 113 5322
- (2013) Chem. Rev. , vol.113 , pp. 5322
- Prier, C.K.¹ Rankic, D.A.² Macmillan, D.W.C.³

53
- 84864453769
- M. A. Ischay M. S. Ament T. P. Yoon Chem. Sci. 2012 3 2807
- (2012) Chem. Sci. , vol.3 , pp. 2807
- Ischay, M.A.¹ Ament, M.S.² Yoon, T.P.³

54
- 84857230386
- J. W. Tucker C. R. J. Stephenson J. Org. Chem. 2012 77 1617
- (2012) J. Org. Chem. , vol.77 , pp. 1617
- Tucker, J.W.¹ Stephenson, C.R.J.²

55
- 84863643233
- J. Xuan W.-J. Xiao Angew. Chem., Int. Ed. 2012 51 6828
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 6828
- Xuan, J.¹ Xiao, W.-J.²

56
- 84864053157
- S. Maity N. Zheng Synlett 2012 23 1851
- (2012) Synlett , vol.23 , pp. 1851
- Maity, S.¹ Zheng, N.²

57
- 79960179626
- Selected articles on photo-CDC reactions
- F. Teplý Collect. Czech. Chem. Commun. 2011 76 859
- (2011) Collect. Czech. Chem. Commun. , vol.76 , pp. 859
- Teplý, F.¹

58
- 79960642484
- Y.-Q. Zou L.-Q. Lu L. Fu N.-J. Chang J. Rong J.-R. Chen W.-J. Xiao Angew. Chem., Int. Ed. 2011 50 7171
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 7171
- Zou, Y.-Q.¹ Lu, L.-Q.² Fu, L.³ Chang, N.-J.⁴ Rong, J.⁵ Chen, J.-R.⁶ Xiao, W.-J.⁷

59
- 79961097289
- D. P. Hari B. Konig Org. Lett. 2011 13 3852
- (2011) Org. Lett. , vol.13 , pp. 3852
- Hari, D.P.¹ Konig, B.²

60
- 81855173304
- M. Rueping S. Zhu R. M. Koenigs Chem. Commun. 2011 47 12709
- (2011) Chem. Commun. , vol.47 , pp. 12709
- Rueping, M.¹ Zhu, S.² Koenigs, R.M.³

61
- 79960504062
- M. Rueping S. Zhu R. M. Koenigs Chem. Commun. 2011 47 8679
- (2011) Chem. Commun. , vol.47 , pp. 8679
- Rueping, M.¹ Zhu, S.² Koenigs, R.M.³

62
- 79960401984
- J. Y. Cheng J. An L.-Q. Lu X.-X. Zhang W.-J. Xiao Chem. Commun. 2011 47 8337
- (2011) Chem. Commun. , vol.47 , pp. 8337
- Cheng, J.Y.¹ An, J.² Lu, L.-Q.³ Zhang, X.-X.⁴ Xiao, W.-J.⁵

63
- 80053531171
- Y. Pan C. W. Kee L. Chen C.-H. Tan Green Chem. 2011 13 2682
- (2011) Green Chem. , vol.13 , pp. 2682
- Pan, Y.¹ Kee, C.W.² Chen, L.³ Tan, C.-H.⁴

64
- 79751515504
- M. Rueping C. Vila R. M. Koenigs K. Poscharny D. C. Fabry Chem. Commun. 2011 47 2360
- (2011) Chem. Commun. , vol.47 , pp. 2360
- Rueping, M.¹ Vila, C.² Koenigs, R.M.³ Poscharny, K.⁴ Fabry, D.C.⁵

65
- 76149096852
- 2 4a (3 mg, 2 mol%) and N-hydroxyphthalimide 2a (33 mg, 0.2 mmol)
- A. G. Condie J. C. Gonzalez-Gomez C. R. J. Stephenson J. Am. Chem. Soc. 2010 132 1464
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 1464
- Condie, A.G.¹ Gonzalez-Gomez, J.C.² Stephenson, C.R.J.³

66
- 33846874104
- I. Hermans P. Jacobs J. Peeters Phys. Chem. Chem. Phys. 2007 9 686
- (2007) Phys. Chem. Chem. Phys. , vol.9 , pp. 686
- Hermans, I.¹ Jacobs, P.² Peeters, J.³

67
- 84897731028
- M. Dinda S. Samanta S. Eringathodi P. K. Ghosh RSC Adv. 2014 4 12252
- (2014) RSC Adv. , vol.4 , pp. 12252
- Dinda, M.¹ Samanta, S.² Eringathodi, S.³ Ghosh, P.K.⁴

68
- 84866424534
- Generation of PINO radical from NHPI see the reviews
- S. Maity N. Zheng Angew. Chem., Int. Ed. 2012 51 9562
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 9562
- Maity, S.¹ Zheng, N.²

69
- 84880906797
- L. Melone C. Punta Beilstein J. Org. Chem. 2013 9 1296
- (2013) Beilstein J. Org. Chem. , vol.9 , pp. 1296
- Melone, L.¹ Punta, C.²

70
- 68849129468
- S. Coseri Catal. Rev. 2009 51 218
- (2009) Catal. Rev. , vol.51 , pp. 218
- Coseri, S.¹

71
- 35148843206
- F. Recupero C. Punta Chem. Rev. 2007 107 3800
- (2007) Chem. Rev. , vol.107 , pp. 3800
- Recupero, F.¹ Punta, C.²

72
- 5144233845
- R. A. Sheldon I. W. C. E. Arends Adv. Synth. Catal. 2004 346 1051
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1051
- Sheldon, R.A.¹ Arends, I.W.C.E.²

73
- 0000434277
- To find experimental evidence on formation of hemiaminal radical, a control experiment was carried out with an idea to identify any pinacol type product if formed by homodimerization of the radical 10 (Scheme 5). But we did not find any dimerized products in the reaction between benzaldehyde and NHPI under optimized condition. However, the radical 10 may still be present in our system, but the oxidation of 10 to ester 3a is faster compare to dimerization. More studies are needed to understand the mechanism of this reaction
- Y. Ishii S. Sakaguchi T. Iwahama Adv. Synth. Catal. 2001 343 393
- (2001) Adv. Synth. Catal. , vol.343 , pp. 393
- Ishii, Y.¹ Sakaguchi, S.² Iwahama, T.³

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