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Volumn 31, Issue 3, 2010, Pages 582-587

Rhodium-catalyzed reductive decyanation of nitriles using hydrosilane as a reducing agent: Scope, mechanism and synthetic application

Author keywords

Carbon carbon bond activation; Hydrosilane; Reductive decyanation; Rhodium catalyst

Indexed keywords

BENZYL CYANIDE; CARBON-CARBON BOND; CYANO GROUPS; HYDROSILANES; ORGANIC SYNTHESIS; REDUCTIVE CLEAVAGE; RHODIUM CATALYSTS; RHODIUM-CATALYZED; SYNTHETIC APPLICATION;

EID: 77951811252     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.03.582     Document Type: Article
Times cited : (37)

References (65)
  • 10
    • 17144377599 scopus 로고    scopus 로고
    • Murahashi, S.-I, Ed.; Thieme: Stuttgart
    • Murahahi, S.-I. In Science of Synthesis; Murahashi, S.-I, Ed.; Thieme: Stuttgart, 2004; Vol. 19, pp 345-402.
    • (2004) Science of Synthesis , vol.19 , pp. 345-402
    • Murahahi, S.-I.1
  • 17
    • 38149100971 scopus 로고    scopus 로고
    • Reviews on transition metal-mediated cleavage of carbon-cyano bonds
    • Reviews on transition metal-mediated cleavage of carbon-cyano bonds: (a) Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 300
    • Tobisu, M.1    Chatani, N.2
  • 21
    • 0037165751 scopus 로고    scopus 로고
    • Silicon-assisted mechanism for the cleavage of carbon-cyano bonds
    • Silicon-assisted mechanism for the cleavage of carbon-cyano bonds: (a) Taw, F. L.; White, P. S.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2002, 124, 4192.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4192
    • Taw, F.L.1    White, P.S.2    Bergman, R.G.3    Brookhart, M.4
  • 32
    • 0042152046 scopus 로고    scopus 로고
    • For related selectivity issues in catalytic reactions of aryl halides withhydrosilanes, see: [Rh]
    • For related selectivity issues in catalytic reactions of aryl halides withhydrosilanes, see: [Rh] (a) Murata, M.; Ishikura, M.; Nagata, M.; Watanabe, S.; Masuda, Y. Org. Lett. 2002, 4, 1843.
    • (2002) Org. Lett. , vol.4 , pp. 1843
    • Murata, M.1    Ishikura, M.2    Nagata, M.3    Watanabe, S.4    Masuda, Y.5
  • 44
    • 42149126132 scopus 로고    scopus 로고
    • For a recent example of a decarboxylation reaction of cyano-acetates in natural product synthesis, see
    • For a recent example of a decarboxylation reaction of cyano-acetates in natural product synthesis, see: Fö rster, S.; Helmchen, G. Synlett 2008, 831.
    • (2008) Synlett , pp. 831
    • Förster, S.1    Helmchen, G.2
  • 45
    • 12344251733 scopus 로고    scopus 로고
    • Reviews on catalytic transformation of alkylhalides, see
    • Reviews on catalytic transformation of alkylhalides, see: (a)Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1525
    • Netherton, M.R.1    Fu, G.C.2
  • 50
    • 77951857525 scopus 로고    scopus 로고
    • Previously, we observed the formation of silyl isocyanide in the rhodium-catalyzed decyanative silylation reaction. See ref 7b
    • Previously, we observed the formation of silyl isocyanide in the rhodium-catalyzed decyanative silylation reaction. See ref 7b.
  • 51
    • 34548175458 scopus 로고    scopus 로고
    • For a recent discussion on this topic, see: See also references therein
    • For a recent discussion on this topic, see: Vyboishchikov, S. F.; Nikonov, G. I. Organometallics 2007, 26, 4160. See also references therein.
    • (2007) Organometallics , vol.26 , pp. 4160
    • Vyboishchikov, S.F.1    Nikonov, G.I.2
  • 52
    • 77951819227 scopus 로고    scopus 로고
    • Such rhodium complexes in higher oxidation states that bear additional silyl groups may account for the formation of silylated byproducts 4, which was observed when less bulky hydrosilanes was employed (See Table 1)
    • Such rhodium complexes in higher oxidation states that bear additional silyl groups may account for the formation of silylated byproducts 4, which was observed when less bulky hydrosilanes was employed (See Table 1).
  • 53
    • 34250613134 scopus 로고    scopus 로고
    • For organocatalytic asymmetric 1, 4-addition reactions, see
    • For organocatalytic asymmetric 1, 4-addition reactions, see: Tso-goeva, S. B. Eur. J. Org. Chem. 2007, 1701.
    • (2007) Eur. J. Org. Chem. , pp. 1701
    • Tsogoeva, S.B.1
  • 56
    • 0034629557 scopus 로고    scopus 로고
    • For other removable ortho-directing groups for C-H bond functionalization reactions, see
    • For other removable ortho-directing groups for C-H bond functionalization reactions, see: (a)Ie, Y.; Chatani, N; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475.
    • (2000) Org. Chem. , vol.65 , pp. 1475
    • Ie, Y.1    Chatani, N.2    Ogo, T.3    Marshall, D.R.4    Fukuyama, T.5    Kakiuchi, F.6    Murai, S.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.