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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, Email:

G.-H. Fang, Z.-J. Yan, M.-Z. Deng, Synthesis, 2006, 1148-1154.

DOI: 10.1055/s-2006-926388


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.

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Key Words

alkenylboronic acids, copper-catalyzed carbomagnesation, Suzuki coupling, stereodefined trisubstituted alkenes, arylation, disubstituted allyl alcohols

ID: J66-Y2006-1030