Tetrahedron

… leaving group at benzylic position: application to a three-component coupling of p-iodobenzyl derivatives, trialkylzincates, and electrophiles leading to functionalized p …

T Harada, T Kaneko, T Fujiwara, A Oku

Index: Harada, Toshiro; Kaneko, Takayuki; Fujiwara, Takayuki; Oku, Akira Tetrahedron, 1998 , vol. 54, # 32 p. 9317 - 9332

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Citation Number: 13

Abstract

A three-component coupling of p-iodobenzyl derivatives, trialkylzincates, and electrophiles is described. Lithium trialkylzincates (R3ZnLi) react with p-iodobenzyl methanesulfonate to give benzylzinc reagents p-RC6H4CH2Zn (L). The reaction proceeds through a mechanism involving initial iodine/zinc exchange and the 1, 2-migration of the resulting arylzincates. The benzylzinc reagents, thus prepared, are subsequently used in coupling reaction with ...