PAPER	Synthesis 2006: 1148-1154   DOI: 10.1055/s-2006-926388
© Georg Thieme Verlag Stuttgart · New York
The First Preparation of 4-Substituted 1,2-Oxaborol-2(5H)-ols and their Palladium­-Catalyzed Cross-Coupling with Aryl Halides to Prepare Stereodefined­ 2,3-Disubstituted Allyl Alcohols
Guo-Hua Fang, Zheng-Jun Yan, Jun Yang, Min-Zhi Deng*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Graduate School of the Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China Fax: +86(21)64166128; e-Mail: dengmz@mail.sioc.ac.cn;
Received 30 September 2005

Abstract

4-Substituted 1,2-oxaborol-2(5H)-ols were prepared through copper-catalyzed carbomagnesation of propargyl alcohol, followed by the transmetallation of magnesium to boron in a one-pot procedure. The Suzuki-Miyaura cross-coupling of these new 2,2-disubstituted alkenylboronic acids with aryl halides afforded stereodefined 2,3-disubstituted allyl alcohols in good to excellent yields.

Key words

alkenylboronic acids - copper-catalyzed carbomagnesation - Suzuki-Miyaura cross-coupling - stereodefined trisubstituted alkenes - disubstituted allyl alcohols