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Volumn 6, Issue 6, 2006, Pages 643-645

Solvent and ligand partition reaction pathways in nickel-mediated carboxylation of methylenecyclopropanes

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBON DIOXIDE; CYCLOPROPANE DERIVATIVE; LIGAND; NICKEL COMPLEX; SOLVENT;

EID: 33646057698     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b515684j     Document Type: Article
Times cited : (37)

References (26)
  • 6
    • 0001500173 scopus 로고    scopus 로고
    • For an example of regiochemical control of the site of cleavage by reaction conditions, see:
    • I. Nakamura Y. Yamamoto Adv. Synth. Catal. 2002 344 111
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 111
    • Nakamura, I.1    Yamamoto, Y.2
  • 15
    • 33646070496 scopus 로고    scopus 로고
    • A mixture of stereoisomers
    • A mixture of stereoisomers
  • 16
    • 33646062788 scopus 로고    scopus 로고
    • Production of 4a was not observed with other amines like DBN, TMEDA, 2,2′-bipyridyl, 1,2-dimethylimidazole and 2-methyl-2-oxazoline
    • Production of 4a was not observed with other amines like DBN, TMEDA, 2,2′-bipyridyl, 1,2-dimethylimidazole and 2-methyl-2-oxazoline
  • 20
    • 33646051897 scopus 로고    scopus 로고
    • 3CN was added to the reaction mixture which was further stirred for an additional 4 h prior to an aqueous workup
    • 3CN was added to the reaction mixture which was further stirred for an additional 4 h prior to an aqueous workup
  • 21
    • 84984242898 scopus 로고
    • Nickel catalysts generally prefer cleavage of the proximal carbon-carbon bond by insertion whereas palladium catalysts prefer that of the distal one:
    • P. Binger M. J. Doyle R. Benn Chem. Ber. 1983 116 1
    • (1983) Chem. Ber. , vol.116 , pp. 1
    • Binger, P.1    Doyle, M.J.2    Benn, R.3
  • 23
    • 0024826463 scopus 로고
    • Regioselective insertion of Zr(ii) into the proximal carbon-carbon bond cis to the phenyl group of 1a has been observed:
    • S. A. Bapuji W. B. Motherwell M. Shipman Tetrahedron Lett. 1989 30 7107
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7107
    • Bapuji, S.A.1    Motherwell, W.B.2    Shipman, M.3
  • 25
    • 33646045517 scopus 로고    scopus 로고
    • Product 4a can result from carboxylation of 1-phenylbuta-1,3-diene, to which 1a may possibly isomerise in the presence of nickel(0). The present reaction conditions, however, caused no carboxylation reaction of 1-phenylbuta-1,3-diene prepared independently
    • Product 4a can result from carboxylation of 1-phenylbuta-1,3-diene, to which 1a may possibly isomerise in the presence of nickel(0). The present reaction conditions, however, caused no carboxylation reaction of 1-phenylbuta-1,3-diene prepared independently
  • 26
    • 33646065575 scopus 로고    scopus 로고
    • The contrasting results obtained with 1g and (arylmethylidene)cyclopropanes 1a-1f are accounted for by assuming the more stable nature of the nickel-benzylic carbon linkage of II
    • The contrasting results obtained with 1g and (arylmethylidene)cyclopropanes 1a-1f are accounted for by assuming the more stable nature of the nickel-benzylic carbon linkage of II


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.