Premium
Carboxylation of Alkylboranes by N‐Heterocyclic Carbene Copper Catalysts: Synthesis of Carboxylic Acids from Terminal Alkenes and Carbon Dioxide
Author(s) -
Ohishi Takeshi,
Zhang Liang,
Nishiura Masayoshi,
Hou Zhaomin
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101769
Subject(s) - carboxylation , carbene , chemistry , catalysis , copper , adduct , medicinal chemistry , organic chemistry , methoxide , alkyl , carbon dioxide
Caught in the act : N‐Heterocyclic carbene copper(I) complexes ( 1 ; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene) serve as an excellent catalyst for the carboxylation of alkylboranes ( 2 ; R=alkyl) with CO 2 to afford a variety of functionalized carboxylic acids ( 3 ) in high yields. A novel copper methoxide/alkylborane adduct ( A ) and its subsequent CO 2 insertion product ( B ) have been isolated and shown to be true active catalyst species.