Palladium-catalyzed insertion reactions of trimethylsilyldiazomethane

Palladium(II) salts catalyze the Kirmse reaction of allylsulfides with trimethylsilyldiazomethane (TMSD) to give homoallyl-sulfides. Similarly, TMSD can intercept ArPdX intermediates generated during Stille couplings to give benzhydryl derivatives. The yields of this process are limited by overinsertion and beta -elimination. insertion and elimination can be harnessed to generate styrenes from benzylic halides in the presence of palladium (0) catalysts. (C) 2001 Elsevier Science Ltd. AU rights reserved.