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Synthesis of oxygen heterocycles via Pd-catalyzed cross-coupling of unsaturated phenols and vinylic halides or triflates

✍ Scribed by R.C. Larock; H. Yang; P. Pace; K. Narayanan; C.E. Russell; S. Cacchi; G. Fabrizi

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 835 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00399-8

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✦ Synopsis

The palladium-catalyzed cross-coupling of o-allytic and o-vinylic phenols with vinylic halides and triflates produces substituted dihydrobenzopyrans and dihydrobenzofurans respectively in good to high yields. The proposed mechanism involves vinylpalladium addition to the olefin, rearrangement to a g-allylpalladium intermediate and subsequent intramolecular nucleophilic displacement of palladium.

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