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

Ohishi Takeshi | Zendy; Zhang Liang | Zendy; Nishiura Masayoshi | Zendy; Hou Zhaomin | Zendy

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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.

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