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Carboxylation of Alkylboranes by N-Heterocyclic Carbene Copper Catalysts: Synthesis of Carboxylic Acids from Terminal Alkenes and Carbon Dioxide

✍ Scribed by Dr. Takeshi Ohishi; Dr. Liang Zhang; Dr. Masayoshi Nishiura; Prof. Dr. Zhaomin Hou

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 309 KB
Volume: 50
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.201101769

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✦ Synopsis

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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## Abstract A broad spectrum of substrates bearing a free allyl moiety can be transformed to carboxylic acids in good to excellent yields and various functionalities are tolerated.