SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 30, 2013, Pages 7860-7864

A mild, one-pot Stadler-Ziegler synthesis of arylsulfides facilitated by photoredox catalysis in batch and continuous-flow

(3) Wang, Xiao a Cuny, Gregory D a,b Noël, Timothy c

a BRIGHAM AND WOMEN S HOSPITAL (United States)

b UNIVERSITY OF HOUSTON (United States)

c EINDHOVEN UNIVERSITY OF TECHNOLOGY (Netherlands)

Author keywords

C S bond formation; microflow chemistry; one pot processes; visible light photoredox catalysis

Indexed keywords

C-S BOND FORMATIONS; CONTINUOUS-FLOW; MICRO-FLOW; MICRO-REACTOR; ONE POT PROCESS; PHOTOREDOX CATALYSIS; SAFETY AND EFFICIENCIES; VISIBLE LIGHT;

CATALYSIS;

CHEMICAL BONDS;

AROMATIC HYDROCARBON; RUTHENIUM; SULFIDE; WATER;

ARTICLE; C S BOND FORMATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; MICROFLOW CHEMISTRY; ONE-POT PROCESSES; PHOTOCHEMISTRY; SYNTHESIS; VISIBLE-LIGHT PHOTOREDOX CATALYSIS;

C S BOND FORMATION; MICROFLOW CHEMISTRY; ONE-POT PROCESSES; VISIBLE-LIGHT PHOTOREDOX CATALYSIS;

CATALYSIS; HYDROCARBONS, AROMATIC; LIGHT; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; RUTHENIUM; SULFIDES; WATER;

EID: 84880358000 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201303483 Document Type: Article

Times cited : (183)

References (71)

1
- 0034687234
- G. Liu, J. T. Link, Z. Pei, E. B. Reilly, S. Leitza, B. Nguyen, K. C. Marsh, G. F. Okasinski, T. W. von Geldern, M. Ormes, K. Fowler, M. Gallatin, J. Med. Chem. 2000, 43, 4025.
- (2000) J. Med. Chem. , vol.43 , pp. 4025
- Liu, G.¹ Link, J.T.² Pei, Z.³ Reilly, E.B.⁴ Leitza, S.⁵ Nguyen, B.⁶ Marsh, K.C.⁷ Okasinski, G.F.⁸ Von Geldern, T.W.⁹ Ormes, M.¹⁰ Fowler, K.¹¹ Gallatin, M.¹²

2
- 0034675702
- Y. Wang, S. Chackalamannil, Z. Hu, J. W. Clader, W. Greenlee, W. Billard, H. Binch, G. Crosby, V. Ruperto, R. A. Duffy, R. McQuade, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2000, 10, 2247.
- (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 2247
- Wang, Y.¹ Chackalamannil, S.² Hu, Z.³ Clader, J.W.⁴ Greenlee, W.⁵ Billard, W.⁶ Binch, H.⁷ Crosby, G.⁸ Ruperto, V.⁹ Duffy, R.A.¹⁰ McQuade, R.¹¹ Lachowicz, J.E.¹²

3
- 17444416142
- L. Llauger, H.-Z. He, J.-N. Kim, J. Aguirre, N. Rosen, U. Peters, P. Davies, G. Chiosis, J. Med. Chem. 2005, 48, 2892.
- (2005) J. Med. Chem. , vol.48 , pp. 2892
- Llauger, L.¹ He, H.-Z.² Kim, J.-N.³ Aguirre, J.⁴ Rosen, N.⁵ Peters, U.⁶ Davies, P.⁷ Chiosis, G.⁸

4
- 58349102704
- D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438
- (2008) Angew. Chem. , vol.120 , pp. 6438
- Surry, D.S.¹ Buchwald, S.L.²

5
- 52049105452
- Angew. Chem. Int. Ed. 2008, 47, 6338
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6338

6
- 12344337315
- B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599.
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1599
- Schlummer, B.¹ Scholz, U.²

7
- 0034738131
- P. J. Fagan, E. Hauptman, R. Shapiro, A. Casalnuovo, J. Am. Chem. Soc. 2000, 122, 5043
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 5043
- Fagan, P.J.¹ Hauptman, E.² Shapiro, R.³ Casalnuovo, A.⁴

8
- 0033549049
- A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4369
- Aranyos, A.¹ Old, D.W.² Kiyomori, A.³ Wolfe, J.P.⁴ Sadighi, J.P.⁵ Buchwald, S.L.⁶

9
- 0033531744
- G. Mann, C. Incarvito, A. L. Rheingold, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 3224.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 3224
- Mann, G.¹ Incarvito, C.² Rheingold, A.L.³ Hartwig, J.F.⁴

10
- 0034251445
- T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205
- (2000) Chem. Rev. , vol.100 , pp. 3205
- Kondo, T.¹ Mitsudo, T.²

11
- 79251500709
- C. C. Eichman, J. P. Stambuli, Molecules 2011, 16, 590.
- (2011) Molecules , vol.16 , pp. 590
- Eichman, C.C.¹ Stambuli, J.P.²

12
- 0001457755
- T. Migita, T. Shimizu, Y. Asami, J.-I. Shiobara, Y. Kato, M. Kosugi, Bull. Chem. Soc. Jpn. 1980, 53, 1385
- (1980) Bull. Chem. Soc. Jpn. , vol.53 , pp. 1385
- Migita, T.¹ Shimizu, T.² Asami, Y.³ Shiobara, J.-I.⁴ Kato, Y.⁵ Kosugi, M.⁶

13
- 3342908633
- M. Murata, S. L. Buchwald, Tetrahedron 2004, 60, 7397
- (2004) Tetrahedron , vol.60 , pp. 7397
- Murata, M.¹ Buchwald, S.L.²

14
- 33644515285
- M. A. Fernández-Rodríguez, Q.-L. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2180
- Fernández-Rodríguez, M.A.¹ Shen, Q.-L.² Hartwig, J.F.³

15
- 0035861768
- G. Y. Li, G. Zheng, A. F. Noonan, J. Org. Chem. 2001, 66, 8677
- (2001) J. Org. Chem. , vol.66 , pp. 8677
- Li, G.Y.¹ Zheng, G.² Noonan, A.F.³

16
- 82955198453
- L. Wang, W.-Y. Zhou, S.-C. Chen, M.-Y. He, Q. Chen, Synlett 2011, 3041
- (2011) Synlett , pp. 3041
- Wang, L.¹ Zhou, W.-Y.² Chen, S.-C.³ He, M.-Y.⁴ Chen, Q.⁵

17
- 84867250920
- P. Guan, C.-S. Cao, Y. Liu, Y.-F. Li, P. He, Q. Chen, G. Liu, Y.-H. Shi, Tetrahedron Lett. 2012, 53, 5987.
- (2012) Tetrahedron Lett. , vol.53 , pp. 5987
- Guan, P.¹ Cao, C.-S.² Liu, Y.³ Li, Y.-F.⁴ He, P.⁵ Chen, Q.⁶ Liu, G.⁷ Shi, Y.-H.⁸

18
- 0042431748
- O. Stadler, Ber. Dtsch. Chem. Ges. 1884, 17, 2075.
- (1884) Ber. Dtsch. Chem. Ges. , vol.17 , pp. 2075
- Stadler, O.¹

19
- 0041429316
- J. H. Ziegler, Ber. Dtsch. Chem. Ges. 1890, 23, 2469.
- (1890) Ber. Dtsch. Chem. Ges. , vol.23 , pp. 2469
- Ziegler, J.H.¹

20
- 0042986312
- G. E. Hilbert, T. B. Johnson, J. Am. Chem. Soc. 1929, 51, 1526.
- (1929) J. Am. Chem. Soc. , vol.51 , pp. 1526
- Hilbert, G.E.¹ Johnson, T.B.²

21
- 0000052190
- A. N. Abeywickrema, A. L. J. Beckwith, J. Am. Chem. Soc. 1986, 108, 8227
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 8227
- Abeywickrema, A.N.¹ Beckwith, A.L.J.²

22
- 84989038869
- S. Perumal, R. Chandrasekaran, V. Vijayabaskar, D. A. Wilson, Magn. Reson. Chem. 1995, 33, 779
- (1995) Magn. Reson. Chem. , vol.33 , pp. 779
- Perumal, S.¹ Chandrasekaran, R.² Vijayabaskar, V.³ Wilson, D.A.⁴

23
- 3042691500
- G. Smith, T. Ruhland, G. Mikkelsen, K. Andersen, C. T. Christoffersen, L. H. Alifrangis, A. Mørk, S. P. Wren, N. Harris, B. M. Wyman, G. Brandt, Bioorg. Med. Chem. Lett. 2004, 14, 4027
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 4027
- Smith, G.¹ Ruhland, T.² Mikkelsen, G.³ Andersen, K.⁴ Christoffersen, C.T.⁵ Alifrangis, L.H.⁶ Mørk, A.⁷ Wren, S.P.⁸ Harris, N.⁹ Wyman, B.M.¹⁰ Brandt, G.¹¹

24
- 33745129787
- G. Smith, G. Mikkelsen, J. Eskildsen, C. Bundgaard, Bioorg. Med. Chem. Lett. 2006, 16, 3981
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 3981
- Smith, G.¹ Mikkelsen, G.² Eskildsen, J.³ Bundgaard, C.⁴

25
- 84880375814
- Patent US 4932999
- Y. Saito, N. Wada, S. Kusano, T. Miyazawa, S. Takahashi, Y. Toyokawa, I. Kajiwara, Patent US 4932999, 1990.
- (1990)
- Saito, Y.¹ Wada, N.² Kusano, S.³ Miyazawa, T.⁴ Takahashi, S.⁵ Toyokawa, Y.⁶ Kajiwara, I.⁷

26
- 0000632143
- G. Petrillo, M. Novi, G. Garbarino, C. Dell'Erba, Tetrahedron Lett. 1985, 26, 6365
- (1985) Tetrahedron Lett. , vol.26 , pp. 6365
- Petrillo, G.¹ Novi, M.² Garbarino, G.³ Dell'Erba, C.⁴

27
- 0001451786
- G. Petrillo, M. Novi, G. Garbarino, C. Dell'Erba, Tetrahedron 1986, 42, 4007
- (1986) Tetrahedron , vol.42 , pp. 4007
- Petrillo, G.¹ Novi, M.² Garbarino, G.³ Dell'Erba, C.⁴

28
- 0033832827
- M. Barbero, I. Degani, N. Diulgheroff, S. Dughera, R. Fochi, M. Migliaccio, J. Org. Chem. 2000, 65, 5600
- (2000) J. Org. Chem. , vol.65 , pp. 5600
- Barbero, M.¹ Degani, I.² Diulgheroff, N.³ Dughera, S.⁴ Fochi, R.⁵ Migliaccio, M.⁶

29
- 0031850093
- M. Barbero, M. Crisma, I. Degani, R. Fochi, P. Perracino, Synthesis 1998, 1171
- (1998) Synthesis , pp. 1171
- Barbero, M.¹ Crisma, M.² Degani, I.³ Fochi, R.⁴ Perracino, P.⁵

30
- 3242736402
- G. K. S. Prakash, D. Hoole, D. S. Ha, J. Wilkinson, G. A. Olah, Arkivoc 2002, 13, 50.
- (2002) Arkivoc , vol.13 , pp. 50
- Prakash, G.K.S.¹ Hoole, D.² Ha, D.S.³ Wilkinson, J.⁴ Olah, G.A.⁵

31
- 85086812787
- For a reported explosion, see:, J. Laquidara, Chem. Eng. News 2001, 79, 6.
- (2001) Chem. Eng. News , vol.79 , pp. 6
- Laquidara, J.¹

32
- 33947303830
- L. Friedman, J. F. Chelbowski, J. Org. Chem. 1968, 33, 1636
- (1968) J. Org. Chem. , vol.33 , pp. 1636
- Friedman, L.¹ Chelbowski, J.F.²

33
- 0034616857
- D. J. Adams, A. Goddard, J. H. Clark, D. J. Macquarrie, Chem. Commun. 2000, 987.
- (2000) Chem. Commun. , pp. 987
- Adams, D.J.¹ Goddard, A.² Clark, J.H.³ Macquarrie, D.J.⁴

34
- 0039721999
- A. Juris, V. Balzani, F. Barigelletti, S. Campagna, P. Belser, A. von Zelewsky, Coord. Chem. Rev. 1988, 84, 85
- (1988) Coord. Chem. Rev. , vol.84 , pp. 85
- Juris, A.¹ Balzani, V.² Barigelletti, F.³ Campagna, S.⁴ Belser, P.⁵ Von Zelewsky, A.⁶

35
- 78650383080
- J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102
- (2011) Chem. Soc. Rev. , vol.40 , pp. 102
- Narayanam, J.M.R.¹ Stephenson, C.R.J.²

36
- 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

37
- 84866379128
- J. Xuan, W.-J. Xiao, Angew. Chem. 2012, 124, 6934
- (2012) Angew. Chem. , vol.124 , pp. 6934
- Xuan, J.¹ Xiao, W.-J.²

38
- 84863643233
- Angew. Chem. Int. Ed. 2012, 51, 6828.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 6828

39
- 83055177179
- D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224
- (2011) Nature , vol.480 , pp. 224
- Nagib, D.A.¹ Macmillan, D.W.C.²

40
- 83055161587
- D. Kalyani, K. B. McMurtrey, S. R. Neufeldt, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18566
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 18566
- Kalyani, D.¹ McMurtrey, K.B.² Neufeldt, S.R.³ Sanford, M.S.⁴

41
- 84874616023
- E. L. Tyson, M. S. Ament, T. P. Yoon, J. Org. Chem. 2013, 78, 2046.
- (2013) J. Org. Chem. , vol.78 , pp. 2046
- Tyson, E.L.¹ Ament, M.S.² Yoon, T.P.³

42
- 80054724785
- T. Noël, S. L. Buchwald, Chem. Soc. Rev. 2011, 40, 5010
- (2011) Chem. Soc. Rev. , vol.40 , pp. 5010
- Noël, T.¹ Buchwald, S.L.²

43
- 80053246708
- M. Oelgemöller, O. Shvydkiv, Molecules 2011, 16, 7522
- (2011) Molecules , vol.16 , pp. 7522
- Oelgemöller, M.¹ Shvydkiv, O.²

44
- 80054031755
- R. L. Hartman, J. P. McMullen, K. F. Jensen, Angew. Chem. 2011, 123, 7642
- (2011) Angew. Chem. , vol.123 , pp. 7642
- Hartman, R.L.¹ McMullen, J.P.² Jensen, K.F.³

45
- 79961218749
- Angew. Chem. Int. Ed. 2011, 50, 7502
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7502

46
- 84874685110
- T. Noël, V. Hessel, ChemSusChem 2013, 6, 405.
- (2013) ChemSusChem , vol.6 , pp. 405
- Noël, T.¹ Hessel, V.²

47
- 84867044781
- J. W. Tucker, Y. Zhang, T. F. Jamison, C. R. J. Stephenson, Angew. Chem. 2012, 124, 4220
- (2012) Angew. Chem. , vol.124 , pp. 4220
- Tucker, J.W.¹ Zhang, Y.² Jamison, T.F.³ Stephenson, C.R.J.⁴

48
- 84859941649
- Angew. Chem. Int. Ed. 2012, 51, 4144
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4144

49
- 84870600958
- F. Lévesque, P. H. Seeberger, Angew. Chem. 2012, 124, 1738
- (2012) Angew. Chem. , vol.124 , pp. 1738
- Lévesque, F.¹ Seeberger, P.H.²

50
- 84857029523
- Angew. Chem. Int. Ed. 2012, 51, 1706
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1706

51
- 84870552816
- R. S. Andrews, J. J. Becker, M. R. Gagne, Angew. Chem. 2012, 124, 4216
- (2012) Angew. Chem. , vol.124 , pp. 4216
- Andrews, R.S.¹ Becker, J.J.² Gagne, M.R.³

52
- 84859949266
- Angew. Chem. Int. Ed. 2012, 51, 4140.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4140

53
- 84887130175
- For a review on the combination of photoredox catalysis and continuous-flow microreactors:, T. Noël, X. Wang, V. Hessel, Chim Oggi 2013, 31 (3), 10.
- (2013) Chim Oggi , vol.31 , pp. 3
- Noël, T.¹ Wang, X.² Hessel, V.³

54
- 26644442183
- J. F. Bunnett, Acc. Chem. Res. 1978, 11, 413
- (1978) Acc. Chem. Res. , vol.11 , pp. 413
- Bunnett, J.F.¹

55
- 0001122514
- C. Dell'Erba, A. Houmam, M. Novi, G. Petrillo, J. Pinson, J. Org. Chem. 1993, 58, 2670.
- (1993) J. Org. Chem. , vol.58 , pp. 2670
- Dell'Erba, C.¹ Houmam, A.² Novi, M.³ Petrillo, G.⁴ Pinson, J.⁵

56
- 84867716997
- D. P. Hari, T. Hering, B. König, Org. Lett. 2012, 14, 5334
- (2012) Org. Lett. , vol.14 , pp. 5334
- Hari, D.P.¹ Hering, T.² König, B.³

57
- 84856823966
- D. P. Hari, P. Schroll, B. König, J. Am. Chem. Soc. 2012, 134, 2958
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 2958
- Hari, D.P.¹ Schroll, P.² König, B.³

58
- 84869189955
- T. Hering, D. P. Hari, B. König, J. Org. Chem. 2012, 77, 10347
- (2012) J. Org. Chem. , vol.77 , pp. 10347
- Hering, T.¹ Hari, D.P.² König, B.³

59
- 84867719861
- P. Schroll, D. P. Hari, B. König, ChemistryOpen 2012, 1, 130
- (2012) ChemistryOpen , vol.1 , pp. 130
- Schroll, P.¹ Hari, D.P.² König, B.³

60
- 37049113623
- H. Cano-Yelo, A. Deronzier, J. Chem. Soc. Perkin Trans. 2 1984, 1093
- (1984) J. Chem. Soc. Perkin Trans. 2 , pp. 1093
- Cano-Yelo, H.¹ Deronzier, A.²

61
- 0013595380
- H. Cano-Yelo, A. Deronzier, Tetrahedron Lett. 1984, 25, 5517
- (1984) Tetrahedron Lett. , vol.25 , pp. 5517
- Cano-Yelo, H.¹ Deronzier, A.²

62
- 84880378120
- For a recent review about this topic:, D. P. Hari, B. König, Angew. Chem. 2013, 125, 4832
- (2013) Angew. Chem. , vol.125 , pp. 4832
- Hari, D.P.¹ König, B.²

63
- 84876580516
- Angew. Chem. Int. Ed. 2013, 52, 4734.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 4734

64
- 0344430086
- For mechanistic studies of the cleavage of disulfide radical anions, see:, S. Antonello, K. Daasbjerg, H. Jensen, F. Taddei, F. Maran, J. Am. Chem. Soc. 2003, 125, 14905.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14905
- Antonello, S.¹ Daasbjerg, K.² Jensen, H.³ Taddei, F.⁴ Maran, F.⁵

65
- 84862908359
- Y. Cheng, J. Yang, Y. Qu, P. Li, Org. Lett. 2012, 14, 98
- (2012) Org. Lett. , vol.14 , pp. 98
- Cheng, Y.¹ Yang, J.² Qu, Y.³ Li, P.⁴

66
- 84857745163
- P. Guillo, O. Hamelin, P. Batat, G. Jonusauskas, N. D. McClenaghan, S. Menage, Inorg. Chem. 2012, 51, 2222
- (2012) Inorg. Chem. , vol.51 , pp. 2222
- Guillo, P.¹ Hamelin, O.² Batat, P.³ Jonusauskas, G.⁴ McClenaghan, N.D.⁵ Menage, S.⁶

67
- 79960651632
- J.-M. Zen, S.-L. Liou, A. S. Kumar, M.-S. Hsia, Angew. Chem. 2003, 115, 597
- (2003) Angew. Chem. , vol.115 , pp. 597
- Zen, J.-M.¹ Liou, S.-L.² Kumar, A.S.³ Hsia, M.-S.⁴

68
- 0037415863
- Angew. Chem. Int. Ed. 2003, 42, 577
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 577

69
- 0038375217
- T. Miyashita, M. Matsuda, Bull. Chem. Soc. Jpn. 1985, 58, 3031
- (1985) Bull. Chem. Soc. Jpn. , vol.58 , pp. 3031
- Miyashita, T.¹ Matsuda, M.²

70
- 48649096440
- T. Miyashita, M. Matsuda, Bull. Chem. Soc. Jpn. 1981, 54, 1740
- (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 1740
- Miyashita, T.¹ Matsuda, M.²

71
- 11844278651
- A. Deronzier, T. J. Meyer, Inorg. Chem. 1980, 19, 2912.
- (1980) Inorg. Chem. , vol.19 , pp. 2912
- Deronzier, A.¹ Meyer, T.J.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.