Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides

Pure and Applied Chemistry

Volumn 86, Issue 3, 2014, Pages 419-424

  Yoshikai, Naohiko ^a   Gao, Ke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

alkylation; C H functionalization; cobalt; imines

Indexed keywords

ALKYLATION; AROMATIC COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; FREE RADICAL REACTIONS; NITROGEN COMPOUNDS;

ALKYLATING AGENTS; ALKYLATION REACTIONS; AROMATIC IMINES; C-H FUNCTIONALIZATION; DIRECTING GROUPS; IMINES; ROOM-TEMPERATURE CONDITIONS; SINGLE ELECTRON TRANSFER;

COBALT;

EID: 84896307506     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1515/pac-2014-5005     Document Type: Conference Paper

References (39)

1. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani. Nature 366, 529 (1993).
2. For recent reviews, see: (a) F. Kakiuchi, T. Kochi. Synthesis 3013 (2008);
3. D. A. Colby R. G. Bergman J. A. Ellman Chem. Rev. 110 624 2010)
4. N. Yoshikai. Synlett 1047 (2011).
5. K. Gao, N. Yoshikai. J. Am. Chem. Soc. 133, 400 (2011);
6. K. Gao, N. Yoshikai. Angew. Chem., Int. Ed. 50, 6888 (2011);
7. Z. Ding, N. Yoshikai. Beilstein J. Org. Chem. 8, 1536 (2012);
8. P.-S. Lee, N. Yoshikai. Angew. Chem., Int. Ed. 52, 1240 (2013);
9. Z. Ding, N. Yoshikai. Angew. Chem., Int. Ed. 52, 8574 (2013);
10. J. Dong, P.-S. Lee, N. Yoshikai. Chem. Lett. 42, 1140 (2013).
11. For branched-selective reactions with styrene derivatives, see refs.
12. [4a,d,f], and the following: (a) Y. Uchimaru. Chem. Commun. 1133 (1999);
13. S. Pan N. Ryu T. Shibata. J. Am. Chem. Soc. 134 17474 2012)
14. For reactions of phenol and anisole derivatives with alkyl olefins, see: (a) L. N. Lewis, J. F. Smith. J. Am. Chem. Soc. 108, 2728 (1986);
15. R. Dorta A. Togni. Chem. Commun. 760 ( 2003
16. Y. Kuninobu, T. Matsuki, K. Takai. J. Am. Chem. Soc. 131 9914 2009.)
17. J. Oyamada, Z. Hou. Angew. Chem., Int. Ed. 51 12828 2012)
18. L. Ackermann. Chem. Commun. 46, 4866 (2010).
19. L. Ackermann, P. Novak, R. Vicente, N. Hofmann. Angew. Chem., Int. Ed. 48, 6045 (2009);
20. L. Ackermann N. Hofmann R. Vicente. Org. Lett. 13 1875 2011)
21. Q. Chen, L. Ilies, E. Nakamura. J. Am. Chem. Soc. 133, 428 (2011);
22. Y. Zhao, G. Chen. Org. Lett. 13, 4850 (2011).
23. K. Gao, N. Yoshikai. J. Am. Chem. Soc. 135, 9279 (2013).
24. K. Gao, N. Yoshikai. Chem. Commun. 48, 4305 (2012).
25. K. Gao, P. S. Lee, C. Long, N. Yoshikai. Org. Lett. 14, 4234 (2012).
26. W. Song, L. Ackermann. Angew. Chem., Int. Ed. 51, 8251 (2012).
27. S. Yang, Z. Li, X. Han, C. He. Angew. Chem., Int. Ed. 48, 3999 (2009).
28. K. Wakabayashi, H. Yorimitsu, K. Oshima. J. Am. Chem. Soc. 123, 5374 (2001);
29. H. Ohmiya, K. Wakabayashi, H. Yorimitsu, K. Oshima. Tetrahedron 62, 2207 (2006);
30. H. Yorimitsu, K. Oshima. Pure Appl. Chem. 78, 441 (2006).
31. H.-F. Klein, S. Camadanli, R. Beck, D. Leukel, U. Flörke. Angew. Chem., Int. Ed. 44, 975 (2005).
32. The results of the stereochemical probes may also be explained by a process involving stereospecific two-electron oxidative addition and reversible b-hydride elimination/re-insertion. However, we prefer the single-electron transfer mechanism at this moment.
33. The fate of this radical probe in related cross-coupling reactions depends on the catalytic system. For example, see ref.
34. [14a] and the following: (a) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura. J. Am. Chem. Soc. 126, 3686 (2004);
35. R. B. Bedford D. W. Bruce R. M. Frost M. Hird. Chem. Commun. 4161 2005
36. R. B. Bedford, M. Betham, D. W. Bruce, S. A. Davis, R. M. Frost, M. Hird. Chem. Commun. 1398 (2006);
37. S. Yasuda, H. Yorimitsu, K. Oshima. Bull. Chem. Soc. Jpn. 81, 287 (2008);
38. O. Vechorkin, V. Proust, X. Hu. J. Am. Chem. Soc. 131, 9756 (2009).
39. Ackermann and co-workers also achieved cobalt-NHC-catalyzed ortho-alkylation of 2-arylpyridines and N-pyridylindoles with alkyl chlorides including a secondary one: B. Punji, W. Song, G. A. Shevchenko, L. Ackermann. Chem.-Eur. J. 19, 10605 (2013).