Cu-deposits on Mg metal surfaces promote electron transfer reactions

Tetrahedron

Volumn 68, Issue 4, 2012, Pages 1085-1091

  Utsumi, Shinya ^a   Katagiri, Toshimasa ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Copper deposited magnesium; Electron transfer; Grignard reagent formation type silylation; Reductive defluorination; Selective dehalogenation

Indexed keywords

BENZENE DERIVATIVE; COPPER; GRIGNARD REAGENT; MAGNESIUM; PERFLUOROALKYL BENZENE; UNCLASSIFIED DRUG;

ARTICLE; DEFLUORINATION; ELECTRON TRANSPORT; MICROSCOPY; PRIORITY JOURNAL; REDUCTION KINETICS; SILYLATION;

EID: 84855444596     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.082     Document Type: Article

References (29)

1. G.S. Silverman, and P.E. Rakita Handbook of Grignard Reagents 1996 Dekker New York, NY
2. C. Einhorn, J. Einhorn, and J.L. Luche Synthesis 1989 787 813
3. J.L. Luche, and J.C. Damiano J. Am. Chem. Soc. 102 1980 7926 7927
4. C.D. Hurd, and C.N. Webb J. Am. Chem. Soc. 49 1927 546 559
5. H. Gilman, J.M. Peterson, and F. Schulze Recl. Trav. Chim. Pays-Bas 47 1928 19 27
6. H. Gilman, and L.L. Heck Bull. Soc. Chim. Fr. 45 1929 250
7. M.S. Kharasch, and O. Reimuth Grignard Reactions of Nonmetallic Substances 1954 Prentice-Hall New York, NY pp 12
8. B.J. Wakefield Organomagnesium Method in Organic Synthesis 1995 Academic London pp 26
9. H. Gilman, and L.L. Heck J. Am. Chem. Soc. 53 1931 377 378
10. H. Gilman, and E.A. Zoellner J. Am. Chem. Soc. 53 1931 1581 1583
11. G. Johnson, and H. Adkins J. Am. Chem. Soc. 53 1931 1520 1523
12. H. Gilman, and N.B.S. John Recl. Trav. Chim. Pays-Bas 49 1930 717 723
13. S. Utsumi, T. Katagiri, and K. Uneyama Tetrahedron 68 2012 580 583
14. I.C. Appleby Chem. Ind. (London) 1971 120
15. E.C. Ashby, and D.M. Al-Fekri J. Organomet. Chem. 390 1990 275 292
16. H.E. Ramsden, A.E. Balint, W.R. Whitford, J.J. Walburn, and R. Cserr J. Org. Chem 22 1957 1202 1206 For studies to avoid the exothermic runaways, see
17. J.L. Leazer Jr., R. Cvetovich, F.-R. Tsay, U. Dolling, T. Vickery, and D. Bachert J. Org. Chem. 68 2003 3695 3698
18. M. Abarbri, F. Dehmel, and P. Knochel Tetrahedron Lett. 40 1999 7449 7453
19. W. Tang, M. Sarvestani, X. Wei, L.J. Nummy, N. Patel, B. Narayanan, D. Byrne, H. Lee, N.K. Yee, and C.H. Senanayake Org. Process Res. Dev. 13 2009 1426 1430
20. Y. Nakamura, and K. Uneyama J. Org. Chem. 72 2007 5894 5897
21. H. Amii, and K. Uneyama Chem. Rev. 109 2009 2119 2183
22. J.F. Garst, and M.P. Soriaga Coord. Chem. Rev. 248 2004 623 652
23. K. Uneyama Organofluorine Chemistry 2006 Blackwell Oxford pp 52-60 and references therein
24. J.D. Roberts, R.L. Webb, and E.A. McElhill J. Am. Chem. Soc. 72 1950 408 411
25. C. Saboureau, M. Troupel, S. Sibille, and J. Perichon J. Chem. Soc., Chem. Commun. 1989 1138 1139
26. P. Clavel, M.-P. Leger-Lambert, C. Biran, F. Serein-Spirau, M. Bordeau, N. Roques, and H. Marzouk Synthesis 1999 829 834
27. P. Clavel, G. Lessene, C. Biran, M. Bordeau, N. Roques, S. Trevin, and D. Montauzon J. Fluorine Chem. 107 2001 301 310
28. H. Amii, Y. Hatamoto, M. Seo, and K. Uneyama J. Org. Chem. 66 2001 7216 7218
29. Discussions on mechanisms of electrochemical benzylic defluorination of benzotrifluoride derivatives, see C.-P. Andrieux, C. Combellas, F. Kanoufi, J.-M. Savéant, and A. Thiébault J. Am. Chem. Soc. 119 1997 9527 9540