Tetrahedron

Palladium-catalyzed insertion reactions of trimethylsilyldiazomethane

KL Greenman, DS Carter, DL Van Vranken

Index: Greenman, Kevin L; Carter, David S; Van Vranken, David L Tetrahedron, 2001 , vol. 57, # 24 p. 5219 - 5225

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Citation Number: 94

Abstract

Palladium (II) salts catalyze the Kirmse reaction of allylsulfides with trimethylsilyldiazomethane (TMSD) to give homoallylsulfides. Similarly, TMSD can intercept ArPdX intermediates generated during Stille couplings to give benzhydryl derivatives. The yields of this process are limited by overinsertion and β-elimination. Insertion and elimination can be harnessed to generate styrenes from benzylic halides in the presence ...