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Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes
Author(s) -
Diemer Vincent,
Begaud Ma,
Leroux Frédéric R.,
Colobert Françoise
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001283
Subject(s) - aryne , regioselectivity , chemistry , steric effects , aryl , coupling reaction , computational chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
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.