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ortho ‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp 2 )–C(sp 3 ) Cross‐Coupling Reactions
Author(s) -
Bigler Raphael,
Aggarwal Varinder K.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711816
Subject(s) - chemistry , chromium , selectivity , coupling reaction , stereochemistry , reaction mechanism , coupling (piping) , medicinal chemistry , organic chemistry , catalysis , mechanical engineering , engineering
A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho ‐lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho ‐selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X‐ray, NMR, and IR experiments to elucidate the reaction mechanism.