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Volumn 46, Issue 24, 2007, Pages 4519-4522

Mild cobalt-catalyzed hydrocyanation of olefins with tosyl cyanide

Author keywords

Cobalt; Cyanides; Homogeneous catalysis; Hydrocyanation; Silanes

Indexed keywords

CATALYSIS; COBALT; CYANIDES; FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL);

EID: 34250772270     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700575     Document Type: Article
Times cited : (200)

References (49)
  • 4
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    • Science of Synthesis, Vol. 19
    • c) J. Podlech, Science of Synthesis, Vol. 19, Georg Thieme, Stuttgart, 2004, pp. 333-344.
    • (2004) Georg Thieme, Stuttgart , pp. 333-344
    • Podlech, J.1
  • 35
    • 0036456046 scopus 로고    scopus 로고
    • For radical cyanations using TsCN see: a
    • For radical cyanations using TsCN see: a) S. Kim, H.-J. Song, Synlett 2002, 2110-2112;
    • (2002) Synlett , pp. 2110-2112
    • Kim, S.1    Song, H.-J.2
  • 37
    • 33748542324 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5847-5849;
    • (2006) Chem. Int. Ed , vol.45 , pp. 5847-5849
    • Angew1
  • 39
    • 34250754149 scopus 로고    scopus 로고
    • dpm = dipivaloylmethanato.
    • dpm = dipivaloylmethanato.
  • 43
    • 0344218074 scopus 로고    scopus 로고
    • For the use of the Mn complex of the corresponding tetramethyl- substituted ligand see: a
    • For the use of the Mn complex of the corresponding tetramethyl- substituted ligand see: a) J. Du Bois, J. Hong, E. M. Carreira, M. W. Day, J. Am. Chem. Soc. 1996, 118, 915-916;
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 915-916
    • Du Bois, J.1    Hong, J.2    Carreira, E.M.3    Day, M.W.4
  • 49
    • 0025943972 scopus 로고    scopus 로고
    • It is interesting to note that ethyl 4-methylbenzenesulfinate was isolated as a side product of the reaction. We observed that TsCN is consumed faster in the reaction with catalyst 5 a than in the reaction employing catalyst 6 a. This could explain why the latter is more efficient in the case of the challenging trisubstituted alkene, ketone, and aldehyde (Table 1, entries 8-10). The reaction of TsCN with alcohols is known to give sulfinate esters in the presence of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO): D. H. R. Barton, J. Cs. Jaszberenyi, E. A. Theodorakis, Tetrahedron 1991, 47, 9167-9178.
    • It is interesting to note that ethyl 4-methylbenzenesulfinate was isolated as a side product of the reaction. We observed that TsCN is consumed faster in the reaction with catalyst 5 a than in the reaction employing catalyst 6 a. This could explain why the latter is more efficient in the case of the challenging trisubstituted alkene, ketone, and aldehyde (Table 1, entries 8-10). The reaction of TsCN with alcohols is known to give sulfinate esters in the presence of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO): D. H. R. Barton, J. Cs. Jaszberenyi, E. A. Theodorakis, Tetrahedron 1991, 47, 9167-9178.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.