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Letter

Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds: Rate Acceleration by Alcohol Additives^†

Supporting Info

Soungyun Mun, Ji-Eon Lee, and Jaesook Yun*

Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon 440-746, Korea

Org. Lett., 2006, 8 (21), pp 4887–4889

DOI: 10.1021/ol061955a

Publication Date (Web): September 23, 2006

†

Dedicated to Professor Eun Lee on the occasion of his 60th birthday.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jaesook@skku.edu

Abstract

The efficient addition of bis(pinacolato)diboron to α,β-unsaturated carbonyl compounds with a copper−diphosphine catalyst has been carried out. A dramatic rate acceleration of the reaction was realized by adding alcohol additives. With use of this procedure, a variety of α,β-unsaturated carbonyl compounds including conjugated substrates at the acid oxidation level such as esters and nitriles were reacted to give to the corresponding β-boryl carbonyl compounds in high yields.

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Published In Issue October 12, 2006
Received August 7, 2006

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Letter

Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds: Rate Acceleration by Alcohol Additives^†