SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn 51, Issue 19, 2015, Pages 4069-4072

Nickel-catalyzed thiolation of unactivated aryl C-H bonds: Efficient access to diverse aryl sulfides

(5) Yan, Sheng Yi a Liu, Yue Jin a Liu, Bin a Liu, Yan Hua a Shi, Bing Feng a

a ZHEJIANG UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; NICKEL;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; ELECTRON TRANSPORT; GAS CHROMATOGRAPHY; OXIDATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOSPECIFICITY; STOICHIOMETRY; SYNTHESIS; TANDEM MASS SPECTROMETRY; THIOLATION;

EID: 84923363848 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c4cc10446c Document Type: Article

Times cited : (144)

References (67)

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

2
- 0345708168
- S. V. Ley A. W. Thomas Angew. Chem., Int. Ed. 2003 42 5400
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5400
- Ley, S.V.¹ Thomas, A.W.²

3
- 0003537148
- Academic Press, New York
- A. Thuillier and P. Metzner, Sulfur Reagents in Organic Synthesis, Academic Press, New York, 1994
- (1994) Sulfur Reagents in Organic Synthesis
- Thuillier, A.¹ Metzner, P.²

4
- 84894601276
- E. A. Ilardi E. Vitaku J. T. Njardarson J. Med. Chem. 2014 57 2832
- (2014) J. Med. Chem. , vol.57 , pp. 2832
- Ilardi, E.A.¹ Vitaku, E.² Njardarson, J.T.³

5
- 84916887444
- For selected recent reviews, see
- C. Shen P. Zhang Q. Sun S. Bai T. S. A. Hor X. Liu Chem. Soc. Rev. 2015 44 291
- (2015) Chem. Soc. Rev. , vol.44 , pp. 291
- Shen, C.¹ Zhang, P.² Sun, Q.³ Bai, S.⁴ Hor, T.S.A.⁵ Liu, X.⁶

6
- 84886793220
- G. Rouquet N. Chatani Angew. Chem., Int. Ed. 2013 52 11726
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 11726
- Rouquet, G.¹ Chatani, N.²

7
- 84865838463
- J. Yamaguchi A. D. Yamaguchi K. Itami Angew. Chem., Int. Ed. 2012 51 8960
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 8960
- Yamaguchi, J.¹ Yamaguchi, A.D.² Itami, K.³

8
- 84865497366
- N. Kuhl M. N. Hopkinson J. Wencel-Delord F. Glorius Angew. Chem., Int. Ed. 2012 51 10236
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 10236
- Kuhl, N.¹ Hopkinson, M.N.² Wencel-Delord, J.³ Glorius, F.⁴

9
- 84863446276
- K. Engle T.-S. Mei M. Wasa J.-Q. Yu Acc. Chem. Res. 2012 45 788
- (2012) Acc. Chem. Res. , vol.45 , pp. 788
- Engle, K.¹ Mei, T.-S.² Wasa, M.³ Yu, J.-Q.⁴

10
- 84868355670
- P. B. Arockiam C. Bruneau P. H. Dixneuf Chem. Rev. 2012 112 5879
- (2012) Chem. Rev. , vol.112 , pp. 5879
- Arockiam, P.B.¹ Bruneau, C.² Dixneuf, P.H.³

11
- 84859783151
- C. Zhang C. Tang N. Jiao Chem. Soc. Rev. 2012 41 3464
- (2012) Chem. Soc. Rev. , vol.41 , pp. 3464
- Zhang, C.¹ Tang, C.² Jiao, N.³

12
- 79952634665
- L. Ackermann Chem. Rev. 2011 111 1315
- (2011) Chem. Rev. , vol.111 , pp. 1315
- Ackermann, L.¹

13
- 79952675758
- C.-L. Sun B.-J. Li Z.-J. Shi Chem. Rev. 2011 111 1293
- (2011) Chem. Rev. , vol.111 , pp. 1293
- Sun, C.-L.¹ Li, B.-J.² Shi, Z.-J.³

14
- 80054972215
- O. Baudoin Chem. Soc. Rev. 2011 40 4902
- (2011) Chem. Soc. Rev. , vol.40 , pp. 4902
- Baudoin, O.¹

15
- 77349090183
- D. A. Colby R. G. Bergman J. A. Ellman Chem. Rev. 2010 110 624
- (2010) Chem. Rev. , vol.110 , pp. 624
- Colby, D.A.¹ Bergman, R.G.² Ellman, J.A.³

16
- 77949381429
- T. W. Lyons M. S. Sanford Chem. Rev. 2010 110 1147
- (2010) Chem. Rev. , vol.110 , pp. 1147
- Lyons, T.W.¹ Sanford, M.S.²

17
- 68949185025
- O. Daugulis H.-Q. Do D. Shabashov Acc. Chem. Res. 2009 42 1074
- (2009) Acc. Chem. Res. , vol.42 , pp. 1074
- Daugulis, O.¹ Do, H.-Q.² Shabashov, D.³

18
- 33744786786
- X. Chen X.-S. Hao C. E. Goodhue J.-Q. Yu J. Am. Chem. Soc. 2006 128 6790
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6790
- Chen, X.¹ Hao, X.-S.² Goodhue, C.E.³ Yu, J.-Q.⁴

19
- 77950210526
- L. Chu X. Yue F.-L. Qing Org. Lett. 2010 12 1644
- (2010) Org. Lett. , vol.12 , pp. 1644
- Chu, L.¹ Yue, X.² Qing, F.-L.³

20
- 77957120001
- S. Zhang P. Qian M. Zhang M. Hu J. Cheng J. Org. Chem. 2010 75 6732
- (2010) J. Org. Chem. , vol.75 , pp. 6732
- Zhang, S.¹ Qian, P.² Zhang, M.³ Hu, M.⁴ Cheng, J.⁵

21
- 84868566088
- L. D. Tran I. Popov O. Daugulis J. Am. Chem. Soc. 2012 134 18237
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 18237
- Tran, L.D.¹ Popov, I.² Daugulis, O.³

22
- 84907966293
- For Cu-catalyzed C-H activation/C-S bond formation of activated C-H bonds, see
- X.-B. Yan P. Gao H.-B. Yang Y.-X. Li X.-Y. Liu Y.-M. Liang Tetrahedron 2014 70 8730
- (2014) Tetrahedron , vol.70 , pp. 8730
- Yan, X.-B.¹ Gao, P.² Yang, H.-B.³ Li, Y.-X.⁴ Liu, X.-Y.⁵ Liang, Y.-M.⁶

23
- 63349097474
- S. Fukuzawa E. Shimizu Y. Atsuumi M. Hagac K. Ogata Tetrahedron Lett. 2009 50 2374
- (2009) Tetrahedron Lett. , vol.50 , pp. 2374
- Fukuzawa, S.¹ Shimizu, E.² Atsuumi, Y.³ Hagac, M.⁴ Ogata, K.⁵

24
- 84961980729
- S. Ranjit R. Lee D. Heryadi C. Shen J. Wu P. Zhang K.-W. Huang X. Liu J. Org. Chem. 2011 76 8999
- (2011) J. Org. Chem. , vol.76 , pp. 8999
- Ranjit, S.¹ Lee, R.² Heryadi, D.³ Shen, C.⁴ Wu, J.⁵ Zhang, P.⁶ Huang, K.-W.⁷ Liu, X.⁸

25
- 79960361665
- A.-X. Zhou X.-Y. Liu K. Yang S.-C. Zhao Y.-M. Liang Org. Biomol. Chem. 2011 9 5456 5462
- (2011) Org. Biomol. Chem. , vol.9 , pp. 5456-5462
- Zhou, A.-X.¹ Liu, X.-Y.² Yang, K.³ Zhao, S.-C.⁴ Liang, Y.-M.⁵

26
- 84903147648
- C. Chen X.-H. Xu B. Yang F.-L. Qing Org. Lett. 2014 16 3372
- (2014) Org. Lett. , vol.16 , pp. 3372
- Chen, C.¹ Xu, X.-H.² Yang, B.³ Qing, F.-L.⁴

27
- 84902959633
- For selected examples of intramolecular C-H thiolation, see
- X. Li Y. Xu W. Wu C. Jiang C. Qi H. Jiang Chem.-Eur. J. 2014 20 7911
- (2014) Chem.-Eur. J. , vol.20 , pp. 7911
- Li, X.¹ Xu, Y.² Wu, W.³ Jiang, C.⁴ Qi, C.⁵ Jiang, H.⁶

28
- 55849152842
- K. Inamoto Y. Arai K. Hiroya T. Doi Chem. Commun. 2008 5529
- (2008) Chem. Commun. , pp. 5529
- Inamoto, K.¹ Arai, Y.² Hiroya, K.³ Doi, T.⁴

29
- 58149186761
- K. Inamoto C. Hasegawa K. Hiroya T. Doi Org. Lett. 2008 10 5147
- (2008) Org. Lett. , vol.10 , pp. 5147
- Inamoto, K.¹ Hasegawa, C.² Hiroya, K.³ Doi, T.⁴

30
- 67649460751
- L. L. Joyce R. A. Batey Org. Lett. 2009 11 2792
- (2009) Org. Lett. , vol.11 , pp. 2792
- Joyce, L.L.¹ Batey, R.A.²

31
- 77956943946
- X.-L. Fang R.-Y. Tang P. Zhong J.-H. Li Synthesis 2009 4183
- (2009) Synthesis , pp. 4183
- Fang, X.-L.¹ Tang, R.-Y.² Zhong, P.³ Li, J.-H.⁴

32
- 82355163559
- H. Wang L. Wang J. Shang X. Li H. Wang J. Gui A. Lei Chem. Commun. 2012 48 76
- (2012) Chem. Commun. , vol.48 , pp. 76
- Wang, H.¹ Wang, L.² Shang, J.³ Li, X.⁴ Wang, H.⁵ Gui, J.⁶ Lei, A.⁷

33
- 84859595775
- S. K. Sahoo A. Banerjee S. Chakraborty B. K. Patel ACS Catal. 2012 2 544
- (2012) ACS Catal. , vol.2 , pp. 544
- Sahoo, S.K.¹ Banerjee, A.² Chakraborty, S.³ Patel, B.K.⁴

34
- 84910006304
- F.-J. Chen G. Liao X. Li J. Wu B.-F. Shi Org. Lett. 2014 16 5644
- (2014) Org. Lett. , vol.16 , pp. 5644
- Chen, F.-J.¹ Liao, G.² Li, X.³ Wu, J.⁴ Shi, B.-F.⁵

35
- 84895454682
- Y. Yang W. Hou L. Qin J. Du H. Feng B. Zhou Y. Li Chem.-Eur. J. 2014 20 416
- (2014) Chem.-Eur. J. , vol.20 , pp. 416
- Yang, Y.¹ Hou, W.² Qin, L.³ Du, J.⁴ Feng, H.⁵ Zhou, B.⁶ Li, Y.⁷

36
- 84897644444
- M. Iwasaki M. Iyanaga Y. Tsuchiya Y. Nishimura W. Li Z. Li Y. Nishihara Chem.-Eur. J. 2014 20 2459
- (2014) Chem.-Eur. J. , vol.20 , pp. 2459
- Iwasaki, M.¹ Iyanaga, M.² Tsuchiya, Y.³ Nishimura, Y.⁴ Li, W.⁵ Li, Z.⁶ Nishihara, Y.⁷

37
- 84916222643
- Selenation
- M. Iwasaki W. Kaneshika Y. Tsuchiya K. Nakajima Y. Nishihara J. Org. Chem. 2014 79 11330
- (2014) J. Org. Chem. , vol.79 , pp. 11330
- Iwasaki, M.¹ Kaneshika, W.² Tsuchiya, Y.³ Nakajima, K.⁴ Nishihara, Y.⁵

38
- 84916201916
- M. Iwasaki Y. Tsuchiya K. Nakajima Y. Nishihara Org. Lett. 2014 16 4920
- (2014) Org. Lett. , vol.16 , pp. 4920
- Iwasaki, M.¹ Tsuchiya, Y.² Nakajima, K.³ Nishihara, Y.⁴

39
- 84893821195
- For Pd-catalyzed sulfonylation, see
- P. Saravanan P. Anbarasan Org. Lett. 2014 16 848
- (2014) Org. Lett. , vol.16 , pp. 848
- Saravanan, P.¹ Anbarasan, P.²

40
- 68049140862
- X. Zhao E. Dimitrijević V. M. Dong J. Am. Chem. Soc. 2009 131 3466
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3466
- Zhao, X.¹ Dimitrijević, E.² Dong, V.M.³

41
- 78751495845
- For reviews on Ni-catalyzed C-H activation of electronically biased arenes and heteroarenes, see
- X. Zhao V. M. Dong Angew. Chem., Int. Ed. 2011 50 932
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 932
- Zhao, X.¹ Dong, V.M.²

42
- 84871242844
- J. Yamaguchi K. Muto K. Itami Eur. J. Org. Chem. 2013 19
- (2013) Eur. J. Org. Chem. , pp. 19
- Yamaguchi, J.¹ Muto, K.² Itami, K.³

43
- 80053563098
- references therein
- Y. Nakao Chem. Rec. 2011 11 242
- (2011) Chem. Rec. , vol.11 , pp. 242
- Nakao, Y.¹

44
- 84876066106
- For pioneering work of the use of bidentate auxiliary, see
- Y. Aihara N. Chatani J. Am. Chem. Soc. 2013 135 5308
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 5308
- Aihara, Y.¹ Chatani, N.²

45
- 25444458063
- V. G. Zaitsev D. Shabashov O. Daugulis J. Am. Chem. Soc. 2005 127 13154
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 13154
- Zaitsev, V.G.¹ Shabashov, D.² Daugulis, O.³

46
- 77949784030
- D. Shabashov O. Daugulis J. Am. Chem. Soc. 2010 132 3965
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 3965
- Shabashov, D.¹ Daugulis, O.²

47
- 0037048663
- For a review, see ref. 4a
- B. D. Dangel K. Godula S. W. Youn B. Sezen D. Sames J. Am. Chem. Soc. 2002 124 11856
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 11856
- Dangel, B.D.¹ Godula, K.² Youn, S.W.³ Sezen, B.⁴ Sames, D.⁵

48
- 80053071150
- H. Shiota Y. Ano Y. Aihara Y. Fukumoto N. Chatani J. Am. Chem. Soc. 2011 133 14952
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 14952
- Shiota, H.¹ Ano, Y.² Aihara, Y.³ Fukumoto, Y.⁴ Chatani, N.⁵

49
- 84892964773
- Y. Aihara N. Chatani J. Am. Chem. Soc. 2014 136 898
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 898
- Aihara, Y.¹ Chatani, N.²

50
- 84896501976
- M. Li J. Dong X. Huang K. Li Q. Wu F. Song J. You Chem. Commun. 2014 50 3944
- (2014) Chem. Commun. , vol.50 , pp. 3944
- Li, M.¹ Dong, J.² Huang, X.³ Li, K.⁴ Wu, Q.⁵ Song, F.⁶ You, J.⁷

51
- 84894495048
- W. Song S. Lackner L. Ackermann Angew. Chem., Int. Ed. 2014 53 2477
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 2477
- Song, W.¹ Lackner, S.² Ackermann, L.³

52
- 84893767226
- X. Wu Y. Zhao H. Ge J. Am. Chem. Soc. 2014 136 1789
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 1789
- Wu, X.¹ Zhao, Y.² Ge, H.³

53
- 84905640161
- X. Wu Y. Zhao H. Ge Chem.-Eur. J. 2014 20 9530
- (2014) Chem.-Eur. J. , vol.20 , pp. 9530
- Wu, X.¹ Zhao, Y.² Ge, H.³

54
- 84905378410
- X. Cong Y. Li Y. Wei X. Zeng Org. Lett. 2014 16 3926
- (2014) Org. Lett. , vol.16 , pp. 3926
- Cong, X.¹ Li, Y.² Wei, Y.³ Zeng, X.⁴

55
- 84919682880
- M. Iyanaga Y. Aihara N. Chatani J. Org. Chem. 2014 79 11933
- (2014) J. Org. Chem. , vol.79 , pp. 11933
- Iyanaga, M.¹ Aihara, Y.² Chatani, N.³

56
- 84919621396
- A. Yokota Y. Aihara N. Chatani J. Org. Chem. 2014 79 11922
- (2014) J. Org. Chem. , vol.79 , pp. 11922
- Yokota, A.¹ Aihara, Y.² Chatani, N.³

57
- 84908638564
- Y. Aihara M. Tobisu Y. Fukumoto N. Chatani J. Am. Chem. Soc. 2014 136 15509
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 15509
- Aihara, Y.¹ Tobisu, M.² Fukumoto, Y.³ Chatani, N.⁴

58
- 84885044834
- F.-J. Chen S. Zhao F. Hu K. Chen Q. Zhang S.-Q. Zhang B.-F. Shi Chem. Sci. 2013 4 4187
- (2013) Chem. Sci. , vol.4 , pp. 4187
- Chen, F.-J.¹ Zhao, S.² Hu, F.³ Chen, K.⁴ Zhang, Q.⁵ Zhang, S.-Q.⁶ Shi, B.-F.⁷

59
- 84890477776
- Q. Zhang K. Chen W.-H. Rao Y.-J. Zhang F.-J. Chen B.-F. Shi Angew. Chem., Int. Ed. 2013 52 13588
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 13588
- Zhang, Q.¹ Chen, K.² Rao, W.-H.³ Zhang, Y.-J.⁴ Chen, F.-J.⁵ Shi, B.-F.⁶

60
- 84903977780
- Q. Zhang X.-S. Yin S. Zhao S.-L. Fang B.-F. Shi Chem. Commun. 2014 50 8353
- (2014) Chem. Commun. , vol.50 , pp. 8353
- Zhang, Q.¹ Yin, X.-S.² Zhao, S.³ Fang, S.-L.⁴ Shi, B.-F.⁵

61
- 84905409253
- X. Li Y.-H. Liu W.-J. Gu B. Liu F.-J. Chen B.-F. Shi Org. Lett. 2014 16 3904
- (2014) Org. Lett. , vol.16 , pp. 3904
- Li, X.¹ Liu, Y.-H.² Gu, W.-J.³ Liu, B.⁴ Chen, F.-J.⁵ Shi, B.-F.⁶

62
- 84920444920
- However, dialkyl disulfides did not react under the standard conditions, probably due to the less oxidizing ability of dialkyl disulfides
- Y.-J. Liu Y.-H. Liu X.-S. Yin W.-J. Gu B.-F. Shi Chem.-Eur. J. 2015 21 205
- (2015) Chem.-Eur. J. , vol.21 , pp. 205
- Liu, Y.-J.¹ Liu, Y.-H.² Yin, X.-S.³ Gu, W.-J.⁴ Shi, B.-F.⁵

63
- 33947487842
- C. N. Yiannios J. V. Karabinos J. Org. Chem. 1963 28 3246
- (1963) J. Org. Chem. , vol.28 , pp. 3246
- Yiannios, C.N.¹ Karabinos, J.V.²

64
- 0001110135
- T. J. Wallace J. Am. Chem. Soc. 1964 86 2018
- (1964) J. Am. Chem. Soc. , vol.86 , pp. 2018
- Wallace, T.J.¹

65
- 0343287875
- See the ESI for details A Ni(i)/Ni(iii) catalytic cycle cannot be ruled out, see
- W. E. Fristad J. R. Peterson Synth. Commun. 1985 15 1
- (1985) Synth. Commun. , vol.15 , pp. 1
- Fristad, W.E.¹ Peterson, J.R.²

66
- 70350721683
- ref. 14e and f During the revision of our manuscript, a related Ni-catalyzed thiolation directed by PIP was reported, see
- A. T. Higgs P. J. Zinn S. J. Simmons M. S. Sanford Organometallics 2009 28 6142
- (2009) Organometallics , vol.28 , pp. 6142
- Higgs, A.T.¹ Zinn, P.J.² Simmons, S.J.³ Sanford, M.S.⁴

67
- 84923165874
- 10.1039/C4CC10431E
- K. Yang Y. Wang X. Chen A. A. Kadi H.-K. Fun H. Sun Y. Zhang H. Lu Chem. Commun. 10.1039/C4CC10431E
- Chem. Commun.
- Yang, K.¹ Wang, Y.² Chen, X.³ Kadi, A.A.⁴ Fun, H.-K.⁵ Sun, H.⁶ Zhang, Y.⁷ Lu, H.⁸

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