Palladium-catalyzed insertion reactions of trimethylsilyldiazomethane

Authors
Greenman, KL Carter, DS Van Vranken, DL
Citation
Kl. Greenman et al., Palladium-catalyzed insertion reactions of trimethylsilyldiazomethane, TETRAHEDRON, 57(24), 2001, pp. 5219-5225
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
24
Year of publication
2001
Pages
5219 - 5225
Database
ISI
SICI code
0040-4020(20010611)57:24<5219:PIROT>2.0.ZU;2-1
Abstract
Palladium(II) salts catalyze the Kirmse reaction of allylsulfides with trim ethylsilyldiazomethane (TMSD) to give homoallyl-sulfides. Similarly, TMSD c an intercept ArPdX intermediates generated during Stille couplings to give benzhydryl derivatives. The yields of this process are limited by overinser tion and beta -elimination. insertion and elimination can be harnessed to g enerate styrenes from benzylic halides in the presence of palladium (0) cat alysts. (C) 2001 Elsevier Science Ltd. AU rights reserved.