Quinonediimine-induced oxidative coupling of organomagnesium reagents

Chemistry - A European Journal

Volumn 20, Issue 3, 2014, Pages 653-656

  Amaya, Toru ^a   Suzuki, Riyo ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C coupling; electron transfer; Grignard reaction; oxidation; redox chemistry

Indexed keywords

1 ,4-ADDITION REACTIONS; C-C COUPLING; ELECTRON TRANSFER; GRIGNARD REACTION; ORGANOMAGNESIUM; OXIDATIVE COUPLINGS; OXIDATIVE HOMOCOUPLING; REDOX CHEMISTRY;

OXIDATION; POLYANILINE;

ADDITION REACTIONS;

EID: 84892365101     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301993     Document Type: Article

References (30)

1. Grignard Reagents: New Developments (Ed.:, H. G. Richey, Jr.,), Wiley, Chichester, 2000.
2. 3 transition-metal oxidants, see:, G. M. Bennett, E. E. Turner, J. Chem. Soc. Trans. 1914, 105, 1057-1062
3. 2:, J. Krizewsky, E. E. Turner, J. Chem. Soc. Trans. 1919, 115, 559-561
4. for AgBr:, J. H. Gardner, P. Borgstrom, J. Am. Chem. Soc. 1929, 51, 3375-3377
5. 3, etc.:, C. C. Vernon, J. Am. Chem. Soc. 1931, 53, 3831-3834
6. 2, etc:, H. Gilman, M. Lichtenwalter, J. Am. Chem. Soc. 1939, 61, 957-959
7. 2:, M. S. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316-2320
8. for TlBr:, A. Mckillop, L. F. Elsom, E. C. Taylor, Tetrahedron 1970, 26, 4041-4050
9. 4:, A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, Tetrahedron 2000, 56, 9601-9605
10. 2 with molecular oxygen:, G. Cahiez, A. Moyeux, J. Buendia, C. Duplais, J. Am. Chem. Soc. 2007, 129, 13788-13789.
11. J.-W. Cheng, F.-T. Luo, Tetrahedron Lett. 1988, 29, 1293-1294
12. T. Nishiyama, T. Seshita, H. Shodai, K. Aoki, H. Kameyama, K. Komura, Chem. Lett. 1996, 549-550
13. A. Krasovskiy, A. Tishkov, V. del Amo, H. Mayr, P. Knochel, Angew. Chem. Int. Ed. 2006, 45, 5010-5014
14. M. S. Maji, T. Pfeifer, A. Studer, Angew. Chem. Int. Ed. 2008, 47, 9547-9550
15. T. Ramnial, S. A. Taylor, J. A. C. Clyburne, C. J. Walsby, Chem. Commun. 2007, 2066-2068.
16. G. Stork, S. R. Dowd, J. Am. Chem. Soc. 1963, 85, 2178-2180
17. J. J. Eisch, Organometallics 2002, 21, 5439-5463
18. P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. Int. Ed. 2003, 42, 4302-4320.
19. A. G. MacDiarmid, Angew. Chem. Int. Ed. 2001, 40, 2581-2590.
20. T. Hirao, S. Fukuhara, J. Org. Chem. 1998, 63, 7534-7535.
21. T. Hirao, M. Higuchi, I. Ikeda, Y. Ohshiro, J. Chem. Soc. Chem. Commun. 1993, 194-195
22. M. Higuchi, I. Ikeda, T. Hirao, J. Org. Chem. 1997, 62, 1072-1078.
23. For accounts, see: a) Redox Systems Under Nano-Space Control (Ed.:, T. Hirao,), Springer, Heidelberg, 2006
24. T. Amaya, T. Hirao, Synlett 2011, 435-448
25. T. Moriuchi, T. Hirao, Acc. Chem. Res. 2012, 45, 347-360.
26. 2O is also reported, see:, C.-C. Han, R. Balakumar, D. Thirumalai, M.-T. Chung, Org. Biomol. Chem. 2006, 4, 3511-3516.
27. H. W. Boone, J. Bryce, T. Lindgren, A. B. Padias, H. K. Hall, Jr., Macromolecules 1997, 30, 2797-2799.
28. Y. Wei, C. Yang, T. Ding, Tetrahedron Lett. 1996, 37, 731-734.
29. H. K. Hall, Jr., A. B. Padias, P. A. Williams, J.-M. Gosau, H. W. Boone, D.-K. Park, Macromolecules 1995, 28, 1-8.
30. A. L. J. Beckwith, W. B. Gara, J. Am. Chem. Soc. 1969, 91, 5689-5691.