SYNTHESIS OF OXYGEN HETEROCYCLES VIA PD-CATALYZED CROSS-COUPLING OF UNSATURATED PHENOLS AND VINYLIC HALIDES OR TRIFLATES

Authors
LAROCK RC YANG H PACE P NARAYANAN K RUSSELL CE CACCHI S FABRIZI G
Citation
Rc. Larock et al., SYNTHESIS OF OXYGEN HETEROCYCLES VIA PD-CATALYZED CROSS-COUPLING OF UNSATURATED PHENOLS AND VINYLIC HALIDES OR TRIFLATES, Tetrahedron, 54(26), 1998, pp. 7343-7356
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
26
Year of publication
1998
Pages
7343 - 7356
Database
ISI
SICI code
0040-4020(1998)54:26<7343:SOOHVP>2.0.ZU;2-S
Abstract
The palladium-catalyzed cross-coupling of o-allylic and o-vinylic phen ols with vinylic halides and triflates produces substituted dihydroben zopyrans and dihydrobenzofurans respectively in good to high yields. T he proposed mechanism involves vinylpalladium addition to the olefin, rearrangement to a pi-allylpalladium intermediate and subsequent intra molecular nucleophilic displacement of palladium. (C) 1998 Elsevier Sc ience Ltd. All rights reserved.