Single-Electron Transfer between CuX2 and Thiols Determined by Extended X-Ray Absorption Fine Structure Analysis: Application in Markovnikov-Type Hydrothiolation of Styrenes

Chemistry - A European Journal

Volumn 22, Issue 51, 2016, Pages 18331-18334

  Yi, Hong ^a   Song, Chunlan ^a   Li, Yiying ^a   Pao, Chih Wen ^c   Lee, Jyh Fu ^c   Lei, Aiwen ^a,b  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

^c NATIONAL SYNCHROTRON RADIATION RESEARCH CENTER   (Taiwan)

Author keywords

copper catalysis; copper reduction; C S bond formation; hydrothiolation; synchrotron

Indexed keywords

CHEMICAL BONDS; COPPER; ELECTRON TRANSITIONS; EXTENDED X RAY ABSORPTION FINE STRUCTURE SPECTROSCOPY; REACTION INTERMEDIATES; STYRENE; SYNCHROTRONS; TRANSITION METALS; X RAY ABSORPTION;

C-S BOND FORMATIONS; COORDINATION SPHERE; COPPER CATALYSIS; COPPER REDUCTION; EXTENDED X-RAY ABSORPTION FINE STRUCTURE ANALYSIS; HYDROTHIOLATION; SINGLE ELECTRON TRANSFER; TRANSITION-METAL-MEDIATED;

COPPER COMPOUNDS;

EID: 85000836749     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201604086     Document Type: Article

References (50)

1. M. H. Gelb, Science 1997, 275–278, 1750;
2. R. Gomez Arrayás, J. C. Carretero, Chem. Commun. 2011, 47, 2207–2211;
3. C. E. Hoyle, C. N. Bowman, Angew. Chem. Int. Ed. 2010, 49, 1540–1573;
4. Angew. Chem. 2010, 122, 1584–1617;
5. J. O. Jeppesen, M. B. Nielsen, J. Becher, Chem. Rev. 2004, 104, 5115–5132;
6. H. Liu, X. Jiang, Chem. Asian J. 2013, 8, 2546–2563;
7. E. M. McGarrigle, E. L. Myers, O. Illa, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841–5883;
8. G. Y. Kreitman, J. C. Danilewicz, D. W. Jeffery, R. J. Elias, J. Agric. Food Chem. 2016, 64, 4105–4113;
9. X. Shi, K. S. Kasprzak, N. S. Dalal, J. Inorg. Biochem. 1993, 50, 211–225;
10. R. C. Smith, V. D. Reed, W. E. Hill, Phosphorus Sulfur Silicon Relat. Elem. 1994, 90, 147–154;
11. I. G. Tarkhanova, M. G. Gantman, A. O. Chizhov, V. V. Smirnov, React. Kinet. Mech. Catal. 2010, 101, 267–278.
12. I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596–1636;
13. S. K. Bur, A. Padwa, Chem. Rev. 2004, 104, 2401–2432;
14. A. Corma, A. Leyva-Perez, M. J. Sabater, Chem. Rev. 2011, 111, 1657–1712;
15. F. Dénès, M. Pichowicz, G. Povie, P. Renaud, Chem. Rev. 2014, 114, 2587–2693;
16. K. Pachamuthu, R. R. Schmidt, Chem. Rev. 2006, 106, 160–187;
17. C. Yin, F. Huo, J. Zhang, R. Martinez-Manez, Y. Yang, H. Lv, S. Li, Chem. Soc. Rev. 2013, 42, 6032–6059.
18. Q. Lu, J. Zhang, F. Wei, Y. Qi, H. Wang, Z. Liu, A. Lei, Angew. Chem. Int. Ed. 2013, 52, 7156–7159;
19. Angew. Chem. 2013, 125, 7297–7300;
20. C. Shen, P. Zhang, Q. Sun, S. Bai, T. S. Hor, X. Liu, Chem. Soc. Rev. 2015, 44, 291–314;
21. H. Wang, Q. Lu, C. Qian, C. Liu, W. Liu, K. Chen, A. Lei, Angew. Chem. Int. Ed. 2016, 55, 1094–1097;
22. Angew. Chem. 2016, 128, 1106–1109;
23. W. Wei, C. Liu, D. Yang, J. Wen, J. You, Y. Suo, H. Wang, Chem. Commun. 2013, 49, 10239–10241;
24. D. B. Williams, M. L. Shaw, M. J. Green, C. W. Holzapfel, Angew. Chem. Int. Ed. 2008, 47, 560–563;
25. Angew. Chem. 2008, 120, 570–573;
26. H. Xi, B. Deng, Z. Zong, S. Lu, Z. Li, Org. Lett. 2015, 17, 1180–1183;
27. R. Xu, J. P. Wan, H. Mao, Y. Pan, J. Am. Chem. Soc. 2010, 132, 15531–15533;
28. Y. Yang, W. Dong, Y. Guo, R. M. Rioux, Green Chem. 2013, 15, 3170;
29. S. F. Zhou, X. Pan, Z. H. Zhou, A. Shoberu, J. P. Zou, J. Org. Chem. 2015, 80, 3682–3687.
30. V. T. Bhat, P. A. Duspara, S. Seo, N. S. Abu Bakar, M. F. Greaney, Chem. Commun. 2015, 51, 4383–4385;
31. O. O. Fadeyi, J. J. Mousseau, Y. Feng, C. Allais, P. Nuhant, M. Z. Chen, B. Pierce, R. Robinson, Org. Lett. 2015, 17, 5756–5759;
32. T. Tamai, K. Fujiwara, S. Higashimae, A. Nomoto, A. Ogawa, Org. Lett. 2016, 18, 2114–2117;
33. E. L. Tyson, M. S. Ament, T. P. Yoon, J. Org. Chem. 2013, 78, 2046–2050;
34. E. L. Tyson, Z. L. Niemeyer, T. P. Yoon, J. Org. Chem. 2014, 79, 1427–1436.
35. Menggenbateer, M. Narsireddy, G. Ferrara, N. Nishina, T. Jin, Y. Yamamoto, Tetrahedron Lett. 2010, 51, 4627–4629;
36. M. A. Savolainen, J. Wu, Org. Lett. 2013, 15, 3802–3804.
37. T. Tamai, A. Ogawa, J. Org. Chem. 2014, 79, 5028–5035;
38. H. Xi, E. Ma, Z. Li, Tetrahedron 2016, 72, 4111–4116.
39. Q. Lu, J. Zhang, P. Peng, G. Zhang, Z. Huang, H. Yi, J. T. Miller, A. Lei, Chem. Sci. 2015, 6, 4851–4854;
40. H. Yi, Z. Liao, G. Zhang, G. Zhang, C. Fan, X. Zhang, E. E. Bunel, C.-W. Pao, J.-F. Lee, A. Lei, Chem. Eur. J. 2015, 21, 18925–18929;
41. J. Rabeah, U. Bentrup, R. Stosser, A. Bruckner, Angew. Chem. Int. Ed. 2015, 54, 11791–11794;
42. Angew. Chem. 2015, 127, 11957–11960;
43. H. Yi, D. Yang, Y. Luo, C.-W. Pao, J.-F. Lee, A. Lei, Organometallics 2016, 35, 1426–1429.
44. R. Bai, G. Zhang, H. Yi, Z. Huang, X. Qi, C. Liu, J. T. Miller, A. J. Kropf, E. E. Bunel, Y. Lan, A. Lei, J. Am. Chem. Soc. 2014, 136, 16760–16763;
45. C. He, G. Zhang, J. Ke, H. Zhang, J. T. Miller, A. J. Kropf, A. Lei, J. Am. Chem. Soc. 2013, 135, 488–493;
46. X. Mu, H. Zhang, P. Chen, G. Liu, Chem. Sci. 2014, 5, 275–280;
47. R. C. Nelson, J. T. Miller, Catal. Sci. Technol. 2012, 2, 461–470;
48. G. Zhang, J. Li, Y. Deng, J. T. Miller, A. J. Kropf, E. E. Bunel, A. Lei, Chem. Commun. 2014, 50, 8709–8711;
49. G. Zhang, H. Yi, G. Zhang, Y. Deng, R. Bai, H. Zhang, J. T. Miller, A. J. Kropf, E. E. Bunel, A. Lei, J. Am. Chem. Soc. 2014, 136, 924–926.
50. E. Boess, D. Sureshkumar, A. Sud, C. Wirtz, C. Fares, M. Klussmann, J. Am. Chem. Soc. 2011, 133, 8106–8169.