Cobalt-catalyzed coupling reaction of alkyl halides with allylic grignard reagents

Angewandte Chemie - International Edition

Volumn 41, Issue 21, 2002, Pages 4137-4139

  Tsuji, Takashi ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Allylation; C C coupling; Cobalt; Cross coupling; Radical reactions

Indexed keywords

ADDITION REACTIONS; CARBON; COBALT; HALIDE MINERALS;

COUPLING REACTIONS;

CATALYSIS;

ALKYL GROUP; ALLYL COMPOUND; COBALT COMPLEX; REAGENT;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; REACTION ANALYSIS;

EID: 0037021014     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021104)41:21<4137::AID-ANIE4137>3.0.CO;2-0     Document Type: Article

References (32)

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6. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
7. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
8. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
9. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
10. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
11. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
12. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
13. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
14. 3 couplings of primary alkyl halides with organometallic reagents. See: a) R. Giovannini, T. Stüdemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515; Angew. Chem. Int. Ed. 1998, 37, 2387-2390; b) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553; c) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85; d) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; e) K. Park, K. Yuan, W. J. Scott, J. Org. Chem. 1993, 58, 4866-4870; f) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; see recent reviews: g) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204; h) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203; Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
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21. Other cobalt-catalyzed coupling reactions, see: a) G. Cahiez, H. Avedissian, Tetrahedron Lett. 1998, 39, 6159-6162; b) H. Avedissian, L. Bérillon, G. Cahiez, P. Knochel, Tetrahedron Lett. 1998, 39, 6163-6166; c) Y. Nishii, K. Wakasugi, Y. Tanabe, Synlett 1998, 67-69; d) M. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316-2320; e) L. F. Elsom, J. D. Hunt, A. McKillop, Organomet. Chem. Rev. A 1972, 8, 135-152.
22. Other cobalt-catalyzed coupling reactions, see: a) G. Cahiez, H. Avedissian, Tetrahedron Lett. 1998, 39, 6159-6162; b) H. Avedissian, L. Bérillon, G. Cahiez, P. Knochel, Tetrahedron Lett. 1998, 39, 6163-6166; c) Y. Nishii, K. Wakasugi, Y. Tanabe, Synlett 1998, 67-69; d) M. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316-2320; e) L. F. Elsom, J. D. Hunt, A. McKillop, Organomet. Chem. Rev. A 1972, 8, 135-152.
23. Other cobalt-catalyzed coupling reactions, see: a) G. Cahiez, H. Avedissian, Tetrahedron Lett. 1998, 39, 6159-6162; b) H. Avedissian, L. Bérillon, G. Cahiez, P. Knochel, Tetrahedron Lett. 1998, 39, 6163-6166; c) Y. Nishii, K. Wakasugi, Y. Tanabe, Synlett 1998, 67-69; d) M. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316-2320; e) L. F. Elsom, J. D. Hunt, A. McKillop, Organomet. Chem. Rev. A 1972, 8, 135-152.
24. Other cobalt-catalyzed coupling reactions, see: a) G. Cahiez, H. Avedissian, Tetrahedron Lett. 1998, 39, 6159-6162; b) H. Avedissian, L. Bérillon, G. Cahiez, P. Knochel, Tetrahedron Lett. 1998, 39, 6163-6166; c) Y. Nishii, K. Wakasugi, Y. Tanabe, Synlett 1998, 67-69; d) M. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316-2320; e) L. F. Elsom, J. D. Hunt, A. McKillop, Organomet. Chem. Rev. A 1972, 8, 135-152.
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28. Asymmetric creation of quaternary carbon centers has attracted much attention. For a review, see: a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066; b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
29. Asymmetric creation of quaternary carbon centers has attracted much attention. For a review, see: a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066; b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
30. Asymmetric creation of quaternary carbon centers has attracted much attention. For a review, see: a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066; b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
31. Asymmetric creation of quaternary carbon centers has attracted much attention. For a review, see: a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066; b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
32. Enantioselective radical reactions were summarized. See: M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163-171.