Organic Letters 2013-04-05

Suzuki-Miyaura cross-coupling of potassium dioxolanylethyltrifluoroborate and aryl/heteroaryl chlorides.

Nicolas Fleury-Brégeot, Daniel Oehlrich, Frederik Rombouts, Gary A Molander

Index: Org. Lett. 15(7) , 1536-9, (2013)

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Abstract

A robust and efficient protocol for the introduction of the dioxolanylethyl moiety onto various aryl and heteroaryl halides has been developed, providing cross-coupling yields up to 93%. Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride provides the key organotrifluoroborate reagent.