Pincer complex-catalyzed redox coupling of alkenes with lodonium salts via presumed palladium(IV) itermediates

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2852-2854

  Aydin, Juhanes ^a   Larsson, Johanna M ^a   Selander, Nicklas ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67649484500     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9010739     Document Type: Article

References (38)

1. (a) Canty, A. J.; Rodemann, T.; Ryan, J. H. Advances in Organometallic Chemistry; Elsevier: New York, 2008; Vol. 55, p 279.
2. (b) Canty, A. J. Acc. Chem. Res. 1992, 25, 83.
3. (c) Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924.
4. (a) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
5. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
6. (c) Daugulis, O.; Zaitsev, V. D. Angew. Chem., Int, Ed. 2005, 44, 4046.
7. (d) Tong, X.; Bellet, M.; Tse, M. K. J. Am. Chem. Soc. 2007, 129, 4906.
8. (e) Muñiz, K.; Hövelmann, C H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
9. (f) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 1119.
10. (g) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148.
11. (h) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690.
12. (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
13. (b) Bielawski, M.; Zhu, M.; Olofsson, B. adv. Synth. Catal. 2007, 349, 2610.
14. (a) Albrecht, M.; v. Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
15. (b) v. d. Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
16. (c) Szabó, K. J. Synlett 2006, 811.
17. (d) Benito-Garagorri, D.; Kirchner, K. Acc. Chem. Res. 2008, 41, 201.
18. (a) Sommer, W. J.; Yu, K.; Sears, J. S.; Ji, Y.; Zheng, X.; Davis, R. J.; Sherrill, C. D.; Jones, C. W.; Week, M. Organometallics 2005, 24, 4351.
19. (b) Eberhard, M. R. Org. Lett. 2004, 6, 2125.
20. (c) Phan, N. T. S.; v. d. Sluys, M.; Jones, C. W. adv. Synth. Catal. 2006, 348, 609.
21. (d) Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855.
22. (a) Lagunas, M.-C.; Gossage, R. A.; Spek, A. L.; v. Koten, G. Organometallics 1998, 17, 731.
23. (b) Canty, A. J.; Rodemann, T.; Skelton, B. W.; White, A. H. Organometallics 2006, 25, 3996.
24. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
25. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315.
26. (c) Zhu, M.; Song, Y.; Cao, Y. Synthesis 2007, 853.
27. (d) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J. J. Org. Chem. 1996, 61, 2604.
28. (e) Pan, D.; Chen, A.; Su, Y.; Zhou, W.; Li, S.; Jia, W.; Xiao, J.; Liu, Q.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2008, 47, 4729.
29. (f) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357.
30. (g) Kurihara, J.; Sodboka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357.
31. (h) Liang, Y.; Luo, S.; Liu, C.; Wu, X.; Ma, Y. Tetrahedron 2000, 56, 2961.
32. (i) Sugioka, K; Uchiyama, M.; Suzuki, T.; Yamazaki, Y. Nippon Kagaku Kaishi 1985, 527.
33. Synthesis and applications of la and analogues:
34. (a) Bedford, R. B.; Draper, S. M.; Scully, P. N.; Welch, S. L. New J. Chem. 2000, 24, 745.
35. (b) Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 1026.
36. (c) Aydin, J.; Kumar, K. S.; Sayah, M. J.; Wallner, O. A.; Szabó, K. J. J. Org. Chem. 2007, 72, 4689.
37. (d) Aydin, J.; Conrad, C. S.; Szabó, K. J. Org. Lett. 2008, 10, 5175.
38. (e) Aydin, J.; Szabó, K. J. Org. Lett. 2008, 10, 2881.