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Volumn 13, Issue 8, 2011, Pages 2050-2053

Nickel-catalyzed reductive cyclization of organohalides

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EID: 79955377314     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200455n     Document Type: Article
Times cited : (55)

References (34)
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  • 2
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  • 4
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    • For reviews on alternate reagents to organotins
    • For reviews on alternate reagents to organotins, see: Baguley, P. A.; Walton, J. C. Angew. Chem., Int. Ed. 1998, 37, 3072.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3072
    • Baguley, P.A.1    Walton, J.C.2
  • 12
    • 17444363662 scopus 로고
    • For examples of nickel catalyses in electrochemical conditions, see
    • For examples of nickel catalyses in electrochemical conditions, see: Ozaki, S.; Matsushita, H.; Ohmori, H. J. Chem. Soc., Chem. Commun. 1992, 1120.
    • (1992) J. Chem. Soc., Chem. Commun. , vol.1120
    • Ozaki, S.1    Matsushita, H.2    Ohmori, H.3
  • 17
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    • For examples of cobalt catalyses using vitamin B12, see
    • Esteves, A. P.; Ferreira, E. C.; Medeiros, M. J. Tetrahedron 2007, 63, 3006. For examples of cobalt catalyses using vitamin B12, see:
    • (2007) J. Tetrahedron , vol.63 , pp. 3006
    • Esteves, A.P.1    Ferreira, E.C.2    Medeiros, M.3
  • 20
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    • For nickel-catalyzed radical reactions under nonelectroreductive conditions for the synthesis of THF derivatives, see
    • For nickel-catalyzed radical reactions under nonelectroreductive conditions for the synthesis of THF derivatives, see: Vaupel, A.; Knochel, P. J. Org. Chem. 1996, 61, 5743.
    • (1996) J. Org. Chem. , vol.61 , pp. 5743
    • Vaupel, A.1    Knochel, P.2
  • 31
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    • For discussion on the exclusive cis-stereoselectivity observed in the radical cyclization of 1a-4a, see ref 8b
    • For discussion on the exclusive cis-stereoselectivity observed in the radical cyclization of 1a-4a, see ref 8b.
  • 32
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    • For a similar tandem radical addition reaction using tributyltin hydride, see:
    • For a similar tandem radical addition reaction using tributyltin hydride, see: Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 303
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  • 33
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    • The same reaction with a 1: 14 (E/Z) mixture of 14a took 7 h to give 1e in 92% yield
    • The same reaction with a 1:14 (E/Z) mixture of 14a took 7 h to give 1e in 92% yield.
  • 34
    • 79955404475 scopus 로고    scopus 로고
    • The reduction in an aprotic solvent required a longer reaction time; the reaction of 14a (3:1 = E/Z) in DMA for 40 h resulted in the formation of 1e in 67% yield with a 29% recovery of 14a as a 1: 3 (E/Z) mixture. No reaction occurred with (Z)-14a
    • The reduction in an aprotic solvent required a longer reaction time; the reaction of 14a (3:1 = E/Z) in DMA for 40 h resulted in the formation of 1e in 67% yield with a 29% recovery of 14a as a 1:3 (E/Z) mixture. No reaction occurred with (Z)-14a.


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