Carboxylation of alkylboranes by N-heterocyclic carbene copper catalysts: synthesis of carboxylic acids from terminal alkenes and carbon dioxide.

Angew Chem Int Ed Engl

Organometallic Chemistry Laboratory and Advanced Catalyst Research Team, RIKEN Advanced Science Institute, Hirosawa, Wako, Saitama, Japan.

Published: August 2011

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.

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http://dx.doi.org/10.1002/anie.201101769DOI Listing

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