Highly selective synthesis of allylated arenes and diarylmethanes via palladium-catalyzed cross coupling involving benzylic derivatives

✍ Scribed by Ei-ichi Negishi; Hajime Matsushita; Nobuhisa Okukado

• Book ID: 104241728
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 235 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90533-7

✦ Synopsis

The Pd-catalyzed cross coupling of either benzylzincs with alkenyl halides or alkenylalanes with benzyl halides provides highly selective and expeditious routes to allylated arenes. We have recently reported a highly selective Pd-catalyzed allylation of alkenyl-and arylmetals. 4 In view of the significance of allylated arenes as part structures of various natural products including vitamins K, 536 coenzymes Q, 536 and maytansinoids,7 we undertook to develop additional selective routes to allylated arenes via cross coupling.

We now report that various allylated arenes can be readily synthesized in a highly stereoand regioselective manner by the Pd-catalyzed cross coupling of either benzylzincs with alkenyl halides or alkenylalanes with benzyl halides (eq 1).

R' ArCHzZnX + 'C=C'