메뉴 건너뛰기




Volumn 128, Issue 24, 2006, Pages 8068-8077

Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: A complement to the Heck reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COBALT; CRYSTALLOGRAPHY; HALIDE MINERALS; ISOMERIZATION; PALLADIUM; REACTION KINETICS;

EID: 33745341181     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061417t     Document Type: Article
Times cited : (198)

References (92)
  • 6
  • 22
    • 1542590356 scopus 로고
    • Transformation with a stoichiometric amount of cobaloximes: (b) Tada, M.; Okabe, M. Chem. Lett. 1980, 201-204.
    • (1980) Chem. Lett. , pp. 201-204
    • Tada, M.1    Okabe, M.2
  • 43
    • 0000782249 scopus 로고    scopus 로고
    • Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, Chapter 3.1
    • (a) Newcomb, M. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, Chapter 3.1.
    • (2001) Radicals in Organic Synthesis , vol.1
    • Newcomb, M.1
  • 55
    • 33745422622 scopus 로고    scopus 로고
    • note
    • 3 groups on the cobalt is likely to be one, yet zero or two is possible.
  • 58
    • 0042379984 scopus 로고    scopus 로고
    • Also see ref 2b
    • (c) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963. Also see ref 2b.
    • (2003) Chem. Rev. , vol.103 , pp. 2945-2963
    • Dounay, A.B.1    Overman, L.E.2
  • 59
    • 0001044222 scopus 로고
    • See ref 19b. However, in most cases, there are no hydrogens that are involved in β-hydride elimination. An exception was the following: Oppolzer, W.; De Vita, R. J. J. Org. Chem, 1991, 56, 6256-6257.
    • (1991) J. Org. Chem , vol.56 , pp. 6256-6257
    • Oppolzer, W.1    De Vita, R.J.2
  • 62
    • 33745373609 scopus 로고    scopus 로고
    • Reference 8e
    • (c) Reference 8e.
  • 63
    • 0025277261 scopus 로고
    • 12-catalyzed reaction of 6-halo-1-hexene derivatives giving vinylcyclopentanes, not methylenecyclopentanes, was reported: (a) Busato, S.; Tinembart, O.; Zhang, Z.; Scheffold, R. Tetrahedron 1990, 46, 3155-3166.
    • (1990) Tetrahedron , vol.46 , pp. 3155-3166
    • Busato, S.1    Tinembart, O.2    Zhang, Z.3    Scheffold, R.4
  • 66
    • 9644260362 scopus 로고    scopus 로고
    • Intramolecular coordination of a tethered alkene to a metal in action often has a considerable effect on the overall transformation. For instance, see: Miller, K. M.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 15342-15343.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15342-15343
    • Miller, K.M.1    Jamison, T.F.2
  • 68
    • 0001688737 scopus 로고
    • For example, Larock reported a palladium-catalyzed cyclization reaction of 14 leading to isopropyl-substituted benzofuran. Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687-4690.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4687-4690
    • Larock, R.C.1    Stinn, D.E.2
  • 71
    • 0842299374 scopus 로고    scopus 로고
    • Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, Chapter 4.4.40
    • (a) Sarkar, T. K. In Science of Synthesis; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2002; Vol. 4, Chapter 4.4.40, pp 837-925.
    • (2002) Science of Synthesis , vol.4 , pp. 837-925
    • Sarkar, T.K.1
  • 72
    • 0001538227 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Chapter 2.2
    • (b) Tamao, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.2, pp 435-480.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 435-480
    • Tamao, K.1
  • 73
    • 0346908681 scopus 로고    scopus 로고
    • Yamamoto, H., Oshima, K., Ed.; Wiley-VCH: Weinheim, Chapter 10.3
    • (c) Miura, K.; Hosomi, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Ed.; Wiley-VCH: Weinheim, 2004; Vol. 2, Chapter 10.3.
    • (2004) Main Group Metals in Organic Synthesis , vol.2
    • Miura, K.1    Hosomi, A.2
  • 76
    • 0032552149 scopus 로고    scopus 로고
    • Cobalt-catalyzed alkenylation with organometallic reagents in THF/NMP: (a) Cahiez, G.; Avedissian, H. Tetrahedron Lett. 1998, 39, 6159-6162.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6159-6162
    • Cahiez, G.1    Avedissian, H.2
  • 78
    • 2442719958 scopus 로고    scopus 로고
    • Cobalt-catalyzed monocoupling reaction of 1,2-dihaloethylenes with silylmethylmagnesium reagents in THF/NMP to yield (E)-3-halo-2-propenylsilanes was reported: (c) Kamachi, T.; Kuno, A.; Matsuno, C.; Okamoto, S. Tetrahedron Lett. 2004, 45, 4677-4679.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4677-4679
    • Kamachi, T.1    Kuno, A.2    Matsuno, C.3    Okamoto, S.4
  • 79
    • 18844429513 scopus 로고    scopus 로고
    • Cobalt-catalyzed cross-coupling reaction of aryl halides with organometallic reagents. (d) Korn, T. J.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 2947-2951.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2947-2951
    • Korn, T.J.1    Knochel, P.2
  • 88
    • 33745336583 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Chapter 4.2
    • Renaud, P. In Radicals in Organic Synthesis: Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, Chapter 4.2.
    • (2001) Radicals in Organic Synthesis , vol.1
    • Renaud, P.1
  • 92
    • 33745392420 scopus 로고    scopus 로고
    • Also see refs 9b, 12j, 12k, and 21
    • (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 302-338. Also see refs 9b, 12j, 12k, and 21.
    • (1996) Chem. Rev. , vol.96 , pp. 302-338
    • Molander, G.A.1    Harris, C.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.