Catalytic Boracarboxylation of Alkynes with Diborane and Carbon Dioxide by an N‑Heterocyclic Carbene Copper Catalyst

By the use of an N-heterocyclic carbene copper(I) complex as a catalyst, the boracarboxylation of various alkynes (e.g., diaryl alkynes, aryl/alkyl alkynes, and phenylacetylene) with a diborane compound and carbon dioxide has been achieved for the first time, affording the α,β-unsaturated β-boralact...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-09, Vol.134 (35), p.14314-14317
Main Authors: Zhang, Liang, Cheng, Jianhua, Carry, Béatrice, Hou, Zhaomin
Format: Article
Language:English
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Summary:By the use of an N-heterocyclic carbene copper(I) complex as a catalyst, the boracarboxylation of various alkynes (e.g., diaryl alkynes, aryl/alkyl alkynes, and phenylacetylene) with a diborane compound and carbon dioxide has been achieved for the first time, affording the α,β-unsaturated β-boralactone derivatives regio- and stereoselectively via a borylcupration/carboxylation cascade. Some important reaction intermediates were isolated and structurally characterized to clarify the reaction mechanism.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3063474