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Designing Cross‐Coupling Reactions using Aryl(trialkyl)silanes
Author(s) -
Minami Yasunori,
Hiyama Tamejiro
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803213
Subject(s) - silanes , aryl , chemistry , alkyl , organic chemistry , alkylation , catalysis , polymer chemistry , silane
Organo(trialkyl)silanes have several advantages, including high stability, low toxicity, good solubility, easy handling, and ready availability compared with heteroatom‐substituted silanes. However, methods for the cross‐coupling of organo(trialkyl)silanes are limited, most probably because of their exceeding robustness. Thus, a practical method for the cross‐coupling of organo(trialkyl)silanes has been a long‐standing challenging research target. This article discusses how aryl(trialkyl)silanes can be used in cross‐coupling reactions. A pioneering example is Cu II catalytic conditions with the use of electron‐accepting aryl‐ or heteroaryl(triethyl)silanes and aryl iodides. The reaction forms biaryls or teraryls. This design concept can be extended to Pd/Cu II ‐catalyzed cross‐coupling polymerization reactions between such silanes and aryl bromides or chlorides and to Cu I ‐catalyzed alkylation using alkyl halides.