期刊
JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 693, 期 2, 页码 283-296出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2007.10.051
关键词
benzylation; palladium catalyst; benzyl-O bond cleavage; olefin synthesis; benzylpalladium carboxylate
Benzylic carboxylates were found to react with Pd(0) complexes bearing tertiary phosphines to give benzylpalladium(II) carboxylate complexes with cleavage of the benzyl-oxygen bond. The benzylpalladium complexes having the trifluoroacetato ligand react with olefins such as ethyl acrylate to give olefin benzylation products. On the basis of these studies a novel palladium-catalyzed benzylation of olefins was developed without using organic halides as the starting materials. The method has another advantage of requiring no base as in the conventional Mizoroki-Heck process using organic halides. The catalytic cycle is proposed to be constituted of elementary processes of (a) oxidative addition of a benzyl carboxylate with C 0 bond cleavage to a Pd(0) complex to give a benzylpalladium carboxylate, (b) olefin insertion into the benzylpalladium bond to give an alkylpalladium complex, and (c) beta-H abstraction to liberate the benzylated olefin. (C) 2007 Elsevier B.V. All rights reserved.
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