These authors contributed equally to this work.
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Communication
Carboxylation of Alkylboranes by N-Heterocyclic Carbene Copper Catalysts: Synthesis of Carboxylic Acids from Terminal Alkenes and Carbon Dioxide†
Article first published online: 7 JUL 2011
DOI: 10.1002/anie.201101769
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Ohishi, T., Zhang, L., Nishiura, M. and Hou, Z. (2011), Carboxylation of Alkylboranes by N-Heterocyclic Carbene Copper Catalysts: Synthesis of Carboxylic Acids from Terminal Alkenes and Carbon Dioxide. Angew. Chem. Int. Ed., 50: 8114–8117. doi: 10.1002/anie.201101769
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This work was partly supported by a Grant-in-aid for Scientific Research (S) (No. 21225004) from the Ministry of Education, Culture, Sports, Science and Technology of Japan and by the Key Project of International Cooperation of the NSFC (20920102030). L.Z. thanks JSPS for a postdoctoral fellowship. We are grateful to Drs. Jianhua Cheng and Shihui Li for help in X-ray analyses, Ms. Karube for elemental analysis, and Ms. Hongo for high resolution mass spectroscopic analysis.
- ‡
These authors contributed equally to this work.
Publication History
- Issue published online: 17 AUG 2011
- Article first published online: 7 JUL 2011
- Manuscript Received: 11 MAR 2011
Funded by
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- NSFC. Grant Number: 20920102030
Keywords:
- alkenes;
- carbon dioxide;
- carboxylation;
- copper;
- N-heterocyclic carbene
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 CO2 to afford a variety of functionalized carboxylic acids (3) in high yields. A novel copper methoxide/alkylborane adduct (A) and its subsequent CO2 insertion product (B) have been isolated and shown to be true active catalyst species.