Facile carbon-sulfur bond cleavage in diarylsulfonium ylides: A catalytic sulfur-to-silicon group transfer

Chemical Communications

Volumn 49, Issue 39, 2013, Pages 4292-4294

  Huang, Xueliang ^a   Goddard, Richard ^a   Maulide, Nuno ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DEUTERIUM; PALLADIUM COMPLEX; SILICON; SULFONIUM YLIDE; SULFUR; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHEMICAL STRUCTURE; COVALENT BOND; STRUCTURE ANALYSIS; TRANSPORT KINETICS;

EID: 84876543778     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc35762c     Document Type: Article

References (38)

1. B. M. Trost and L. S. Melvin, Sulfur Ylides; Academic Press, New York, 1975
2. A.-H. Li, L.-X. Dai, V. K. Aggarwal: Chem. Rev. 1997 97:2341
3. V. K. Aggarwal, C. L. Winn: Acc. Chem. Res. 2004 37:611
4. Y. Tang, S. Ye, X.-L. Sun: Synlett 2005 2720
5. E. M. McGarrigle, E. L. Meyers, O. Illa, M. A. Shaw, S. L. Riches, V. K. Aggarwal: Chem. Rev. 2007 107:5841
6. B. M. Trost: J. Am. Chem. Soc. 1966 88:1587
7. P. Müller, D. Fernandez, P. Nury, J.-C. Rossier: Helv. Chim. Acta 1999 82:935
8. M. Gandelman, B. Rybtchinski, N. Ashkenazi, R. M. Gauvin, D. Milstein: J. Am. Chem. Soc. 2001 123:5372
9. M. Gandelman, K. M. Naing, B. Rybtchinski, E. Poverenov, Y. Ben-David, N. Ashkenazi, R. M. Gauvin, D. Milstein: J. Am. Chem. Soc. 2005 127:15265
10. S. A. Stoffregen, M. Heying, W. S. Jenks: J. Am. Chem. Soc. 2007 129:15746
11. P. Müller, D. Fernandez, P. Nury, J.-C. Rossier: J. Phys. Org. Chem. 1998 11:321
12. T. Cohen, G. Herman, T. M. Chapman, D. Kuhn: J. Am. Chem. Soc. 1974 96:5627
13. B. Cimetière, M. Julia: Synlett 1991 271
14. P. Müller, D. Fernandez, P. Nury, J.-C. Rossier: Helv. Chim. Acta 1999 82:935
15. S. Kramer, T. Skrydstrup: Angew. Chem., Int. Ed. 2012 51:4681
16. M. P. Doyle: Chem. Rev. 1986 86:919
17. M. P. Doyle, J. H. Griffin, M. S. Chinn, D. V. Leusen: J. Org. Chem. 1984 49:1917
18. V. Nair, S. M. Nair, S. Mathai, J. Liebscher, B. Ziemer, K. Narsimulu: Tetrahedron Lett. 2004 45:5759
19. K. K. Ellis-Holder, B. P. Peppers, A. Y. Kovalevsky, S. T. Diver: Org. Lett. 2006 8:2511
20. A. J. P. Mortimer, A. E. Aliev, D. A. Tocher, M. J. Porter: Org. Lett. 2008 10:5477
21. J.-P. Qu, Z.-H. Xu, J. Zhou, C.-L. Cao, X.-L. Sun, L.-X. Dai, Y. Tang: Adv. Synth. Catal. 2009 351:308
22. X. Huang, R. Goddard, N. Maulide: Angew. Chem., Int. Ed. 2010 49:8979
23. X. Huang, B. Peng, M. Luparia, L. F. R. Gomes, L. F. Veiros, N. Maulide: Angew. Chem., Int. Ed. 2012 51:8886
24. M. Tudge, M. Tamiya, C. Savarin, G. R. Humphrey: Org. Lett. 2006 8:565
25. Y.-J. Guo, R.-Y. Tang, J.-H. Li, P. Zhong, X.-G. Zhang: Adv. Synth. Catal. 2009 351:2615
26. J. S. Yadav, B. V. S. Reddy, Y. J. Reddy, K. Praneeth: Synthesis 2009 1520
27. X.-L. Fang, R.-Y. Tang, P. Zhong, J.-H. Li: Synthesis 2009 4183
28. Z. Li, J. Hong, X. Zhou: Tetrahedron 2011 67:3690
29. D. Huang, J. Chen, W. Dan, J. Ding, M. Liu, H. Wu: Adv. Synth. Catal. 2012 354:2123
30. B. Marciniec, Hydrosilylation, Advances in Silicon Science, Springer, 2009
31. H. M. Gillis, L. Greene, A. Thompson: Synlett 2009 112
32. M. A. Rashid, N. Rasool, M. Adeel, H. Reinke, C. Fischer, P. Langer: Tetrahedron 2008 64:3782
33. B. M. Trost, F. D. Toste: J. Am. Chem. Soc. 1996 118:6305
34. B. M. Trost, F. D. Toste, K. Greenman: J. Am. Chem. Soc. 2003 125:4518
35. R. Nakao, H. Rhee, Y. Uozumi: Org. Lett. 2005 7:163
36. S. K. Pandey, A. E. Greene, J.-F. Poisson: J. Org. Chem. 2007 72:7769
37. J. M. Brunel: Synlett 2007 330
38. R. Shen, T. Chen, Y. Zhao, R. Qiu, Y. Zhou, S. Yin, X. Wang, M. Goto, L.-B. Han: J. Am. Chem. Soc. 2011 133:17037