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Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated ketones under microwave irradiation

Viera Poláčková, Vladimír Bariak, Radovan Šebesta, and Štefan Toma

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15 Bratislava, Slovakia

 

E-mail: radovan.sebesta@fns.uniba.sk

Abstract: The Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated cyclic ketones was studied under controlled microwave irradiation conditions. A variety of catalysts, bases and solvents was explored in order to achieve optimum yields in the shortest possible reaction time. Under optimised conditions (Pd(OAc)2/2,2′-bipyridine and KF in a mixture of toluene, water, and acetic acid and 10 min microwave irradiation), a range of arylboronic acids was successfully added to several cyclic enones. With chiral phosphane ligands, a promising enantioselectivity was obtained (85 % ee).

Keywords: palladium – catalysis – Michael addition – arylboronic acid – microwave irradiation

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-011-0016-3

 

Chemical Papers 65 (3) 338–344 (2011)

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