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Copper‐Catalyzed Coupling of Triaryl‐ and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations
Author(s) -
Thapa Surendra,
Gurung Santosh K.,
Dickie Diane A.,
Giri Ramesh
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407586
Subject(s) - reagent , aryl , chemistry , catalysis , nucleophile , halide , steric effects , combinatorial chemistry , coupling reaction , organic chemistry , copper , catalytic cycle , medicinal chemistry , alkyl
An efficient copper(I)‐catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol %) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations. The reaction tolerates a variety of functional groups and sterically hindered substrates. Furthermore, preliminary mechanistic studies that entailed the synthesis and characterization of potential reaction intermediates offered a glimpse of the elementary steps that constitute the catalytic cycle.