Single-electron-transfer-induced coupling of arylzinc reagents with aryl and alkenyl halides

Angewandte Chemie - International Edition

Volumn 53, Issue 2, 2014, Pages 521-525

  Shirakawa, Eiji ^a,c   Tamakuni, Fumiko ^a   Kusano, Eugene ^a   Uchiyama, Nanase ^a   Konagaya, Wataru ^a   Watabe, Ryo ^a   Hayashi, Tamio ^b  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

^c NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

anion radicals; aromatic compounds; biaryls; C C coupling; single electron transfer

Indexed keywords

ANION RADICALS; ARYLZINC REAGENTS; BIARYLS; C-C COUPLING; CROSS-COUPLING PRODUCTS; SINGLE ELECTRON TRANSFER; STYRENE DERIVATIVES; TRANSITION-METAL CATALYSIS;

AROMATIC COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; METAL HALIDES; STYRENE; TRANSITION METALS;

FREE RADICAL REACTIONS;

EID: 84891802591     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308200     Document Type: Article

References (32)

1. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469
2. Metal-Catalyzed Cross-Coupling Reactions, Vol.1-2, 2 nd ed., (Eds.: A. deMeijere, F. Diederich,), Wiley-VCH, Weinheim, 2004.
3. E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823; For reviews, see
4. E. Negishi, Acc. Chem. Res. 1982, 15, 340-348
5. E. Negishi, in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol.1 (Eds.:, E. Negishi, A. deMeijere,), Wiley-Interscience, New York, 2002, chap.III. 2.1, pp. 229-247.
6. E. Shirakawa, Y. Hayashi, K. Itoh, R. Watabe, N. Uchiyama, W. Konagaya, S. Masui, T. Hayashi, Angew. Chem. 2012, 124, 222-225
7. Angew. Chem. Int. Ed. 2012, 51, 218-221; for the mechanistic aspects, see
8. N. Uchiyama, E. Shirakawa, T. Hayashi, Chem. Commun. 2013, 49, 364-366.
9. For the coupling with alkenyl halides:, E. Shirakawa, R. Watabe, T. Murakami, T. Hayashi, Chem. Commun. 2013, 49, 5219-5221.
10. A. Scrivanti, V. Beghetto, M. Bertoldini, U. Matteoli, Eur. J. Org. Chem. 2012, 264-268
11. M. Ueda, K. Nishimura, R. Kashima, I. Ryu, Synlett 2012, 1085-1089.
12. K. Takagi, Chem. Lett. 1993, 469-472
13. M. Amano, A. Saiga, R. Ikegami, T. Ogata, K. Takagi, Tetrahedron Lett. 1998, 39, 8667-8668.
14. J. E. Fleckenstein, K. Koszinowski, Organometallics 2011, 30, 5018-5026; for examples reported by others of enhancement of the reactivities of organozinc reagents by addition of LiCl, see
15. A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 118, 6186-6190
16. Angew. Chem. Int. Ed. 2006, 45, 6040-6044
17. H. Ren, G. Dunet, P. Mayer, P. Knochel, J. Am. Chem. Soc. 2007, 129, 5376-5377
18. N. Boudet, S. Sase, P. Sinha, C.-Y. Liu, A. Krasovskiy, P. Knochel, J. Am. Chem. Soc. 2007, 129, 12358-12359
19. A. Metzger, M. A. Schade, P. Knochel, Org. Lett. 2008, 10, 1107-1110
20. H. Ochiai, M. Jang, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 2681-2683
21. G. T. Achonduh, N. Hadei, C. Valente, S. Avola, C. J. O'Brien, M. G. Organ, Chem. Commun. 2010, 46, 4109-4111
22. D. R. Armstrong, W. Clegg, P. García-Álvarez, A. R. Kennedy, M. D. McCall, L. Russo, E. Hevia, Chem. Eur. J. 2011, 17, 8333-8341.
23. 2 (X=halogen) generated upon transmetalation might alter the structure of the zincate derived from PhZnX and LiCl and thus affect its reactivity. For a report on the effect of the method used to prepare the arylzinc halides on the efficiency of the reaction, see:, L. Jin, C. Liu, J. Liu, F. Hu, Y. Lan, A. S. Batsanov, J. A. K. Howard, T. B. Marder, A. Lei, J. Am. Chem. Soc. 2009, 131, 16656-16657.
24. Y. Saheki, K. Sasada, N. Satoh, K. Kawaichi, K. Negoro, Chem. Lett. 1987, 2299-2300
25. N. Metzler, H. Noeth, M. Schmidt, A. Z. Treitl, Z. Naturforsch. B 1994, 49, 1448-1451.
26. RN1 reaction, see:, G. A. Russell, R. K. Norris, E. J. Panek, J. Am. Chem. Soc. 1971, 93, 5839-5845.
27. M. A. Nazareno, R. A. Rossi, Tetrahedron Lett. 1994, 35, 5185-5188
28. Y. Zhang, H. Guo, Heteroat. Chem. 2001, 12, 539-541.
29. C. Costentin, M. Robert, J.-M. Savéant, J. Am. Chem. Soc. 2004, 126, 16051-16057
30. N. Takeda, P. V. Poliakov, A. R. Cook, J. R. Miller, J. Am. Chem. Soc. 2004, 126, 4301-4309.
31. A. N. Abeywickrema, A. L. J. Beckwith, J. Chem. Soc. Chem. Commun. 1986, 464-465
32. H. Yasuda, Y. Uenoyama, O. Nobuta, S. Kobayashi, I. Ryu, Tetrahedron Lett. 2008, 49, 367-370; consequently, if the aryl radical is involved as an intermediate, it must undergo cyclization at least in part. For a detailed discussion, see Equation(4) of Ref.[3b] and its explanatory sentences. Technology