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Volumn 42, Issue 41, 2003, Pages 5051-5053

A General Method for the Direct α-Arylation of Nitriles with Aryl Chlorides

Author keywords

Arylation; Homogeneous catalysis; Nitriles; P ligands; Palladium

Indexed keywords

AROMATIC HYDROCARBONS; ELECTRONS; PALLADIUM;

EID: 0242291910     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351954     Document Type: Article
Times cited : (145)

References (44)
  • 11
    • 0001518849 scopus 로고
    • When activated aryl halides including fluorides, chlorides, bromides, and iodides were used as substrates, the uncatalyzed coupling of nitriles focused only on phenylacetonitrile derivatives and cyanoacetates as reactants: a) M. Makosza, M. Jagusztyn-Grochowska, M. Ludwikow, M. Jawdosiuk, Tetrahedron 1974, 30, 3723-3735;
    • (1974) Tetrahedron , vol.30 , pp. 3723-3735
    • Makosza, M.1    Jagusztyn-Grochowska, M.2    Ludwikow, M.3    Jawdosiuk, M.4
  • 17
    • 0033950371 scopus 로고    scopus 로고
    • For unactivated aryl fluorides, limitations were encountered on the structures of the nitriles found suitable for reaction. For example, only the anions of secondary nitriles underwent substitution, and ethyl cyanoacetate and primary nitriles were unreactive: S. Caron, E. Vazquez, J. M. Wojcik, J. Am. Chem. Soc. 2000, 122, 712-713.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 712-713
    • Caron, S.1    Vazquez, E.2    Wojcik, J.M.3
  • 26
    • 0242275771 scopus 로고    scopus 로고
    • note
    • Aldrich and Fluka for 1a, 1b, 1c; Strem for 1b.
  • 38
    • 0242275768 scopus 로고    scopus 로고
    • note
    • 4, filtered, concentrated in vacuo, and purified by column chromatography on silica gel eluting with ethl acetate/hexane or dichloromethane/hexane.
  • 39
    • 0242339186 scopus 로고    scopus 로고
    • note
    • Control experiments showed that either in the absence of a Pd source or in the absence of proazaphosphatrane, no reaction was observed.
  • 40
    • 0242275770 scopus 로고    scopus 로고
    • note
    • 3, no reaction was observed.
  • 41
    • 0242339187 scopus 로고    scopus 로고
    • note
    • A 1:2 palladium-to-ligand ratio gave faster reaction rates and better product yields than a 1:1 ratio.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.