Aryliodine(III) diacetates as substrates for Pd-Ag catalyzed arylation of alkenes

Tetrahedron Letters

Volumn 52, Issue 33, 2011, Pages 4327-4329

  Evdokimov, Nikolai M ^a   Kornienko, Alexander ^a   Magedov, Igor V ^a  

^a NEW MEXICO INSTITUTE OF MINING AND TECHNOLOGY   (United States)

Author keywords

Cross coupling; Hypervalent iodine; Palladium; Synthesis in water

Indexed keywords

ACETOACETIC ACID; ALKENE DERIVATIVE; IODIDE; OXYGEN; PALLADIUM; SILVER; SOLVENT; WATER;

ARTICLE; ARYLATION; CATALYSIS; COLUMN CHROMATOGRAPHY; CROSS COUPLING REACTION; DECOMPOSITION; ELECTRON; HECK REACTION;

EID: 79960279710     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.051     Document Type: Article

References (28)

1. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
2. S.R. Dubbaka, and P. Vogel Angew. Chem., Int. Ed. 44 2005 7674
3. X. Zhou, J. Luo, J. Liu, S. Peng, and G.-J. Deng Org. Lett. 13 2011 1432
4. P. Hu, J. Kan, W. Su, and M. Hong Org. Lett. 11 2009 2341
5. J. Le Bras, and J. Muzart Chem. Rev. 111 2011 1170
6. C.S. Yeung, and V.M. Dong Chem. Rev. 111 2011 1250 and references cited therein
7. V.V. Zhdankin, and P.J. Stang Chem. Rev. 108 2008 5299
8. N.R. Deprez, and M.S. Sanford Inorg. Chem. 46 2007 1924
9. A. Rodriguez, and W.J. Moran Eur. J. Org. Chem. 2009 1313
10. A.D. Satterfield, A. Kubota, and M.S. Sanford Org. Lett. 13 2011 1076
11. D. Pan, M. Yu, M. Chen, and N. Jiao Chem. Asian J. 5 2010 1090
12. T. Jeffery Tetrahedron Lett. 32 1991 2121
13. Y. Su, and N. Jiao Org. Lett. 11 2009 2980
14. D. Pan, and N. Jiao Synlett 2010 1577
15. Notably, iodoaryl diacetates were used as reactants in catalyst-free Suzuki-type coupling: J. Yan, Z. Zhou, and M. Zhu Tetrahedron Lett. 46 2005 8173
16. and in a domino carbopalladation/C-H activation/C-C bond forming process: S. Tang, P. Peng, P. Zhong, and J.-H. Li J. Org. Chem. 73 2008 5476
17. T. Yoneyama, and R.H. Crabtree J. Mol. Catl. A: Chem. 108 1996 35
18. Yang Li, D. Song, and V.M. Dong J. Am. Chem. Soc. 130 2008 2962
19. T. Vogler, and A. Studer Synthesis 2008 1979
20. M.D. Hossain, and T. Kitamura J. Org. Chem. 70 2005 6984
21. A.R. Dick, J.W. Kampf, and M.S. Sanford J. Am. Chem. Soc. 127 2005 12790
22. J. Racowski, A.R. Dick, and M.S. Sanford J. Am. Chem. Soc. 131 2009 10974
23. D.C. Powers, M.A.L. Geibel, J.E.M.N. Klein, and T. Ritter J. Am. Chem. Soc. 131 2009 17050
24. About thermal decomposition of aryl iodine diacetates, see: J.E. Leffer, and L.J. Story J. Am. Chem. Soc. 89 1967 2333
25. L. Brotto, F. Battistutta, L. Tat, P. Comuzzo, and R. Zironi J. Agric. Food Chem. 58 2010 3567
26. Z. Tao, J. Goodisman, and A.-K. Souid J. Phys. Chem. 112 2008 1511
27. D. Pan, A. Chen, Y. Su, W. Zhou, S. Li, W. Jia, J. Xiao, Q. Liu, L. Zhang, and N. Jiao Angew. Chem., Int. Ed. 47 2008 4729
28. D.-W. Chen, and M. Ochiai J. Org. Chem. 64 1999 6804