期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 2, 页码 341-354出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001283
关键词
Arynes; Cross-coupling; Bromine; Biaryls; Regioselectivity; Lithiation
资金
- Centre National de la Recherche Scientifique (CNRS)
- Ministere de l'Education Nationale et de la Recherche
- Agence Nationale pour la Recherche (ANR) [07-BLAN-0292-01]
Tri- and tetrasubstituted ortho-bromobiaryls have been synthesized in good-to-excellent yields by aryne cross-coupling reactions starting from 1,3-dimethoxybenzene and functionalized 1,2-dibromobenzenes. This study outlines the influence of the 1,2-dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl-aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross-coupling reactions.
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