Synthesis

Conjugate additions of α, β-unsaturated ketones with arylzinc species that form in situ from diethylzinc and arylboronic acids

L Dong, YJ Xu, LZ Gong, AQ Mi, YZ Jiang

Index: Dong, Lin; Xu, Yan-Jun; Gong, Liu-Zhu; Mi, Ai-Qiao; Jiang, Yao-Zhong Synthesis, 2004 , # 7 p. 1057 - 1061

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Citation Number: 7

Abstract

We first studied the reaction of chalcone (1a) with the combination of phenylboronic acid and diethylzinc. The phenylzinc species was prepared by stirring a mixture of phenylboronic acid and a 3-fold excess of Et 2 Zn in toluene at 60 °C under argon for 12 hours. It was then reacted with chalcone (1a) at 0 °C to give 3a in 92% yield (Table [1] , entry 1). [6] The use of several commercial arylboronic acids 2a-f and an ester 2g in the 1,4-addition of chalcone (1a) under the ...