SYNTHESIS OF NITROGEN-HETEROCYCLES VIA PD-CATALYZED CROSS-COUPLING OFO-ALKENYL ANILIDES WITH VINYLIC HALIDES AND TRIFLATES

Authors
LAROCK RC PACE P YANG H RUSSELL CE CACCHI S FABRIZI G
Citation
Rc. Larock et al., SYNTHESIS OF NITROGEN-HETEROCYCLES VIA PD-CATALYZED CROSS-COUPLING OFO-ALKENYL ANILIDES WITH VINYLIC HALIDES AND TRIFLATES, Tetrahedron, 54(34), 1998, pp. 9961-9980
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
34
Year of publication
1998
Pages
9961 - 9980
Database
ISI
SICI code
0040-4020(1998)54:34<9961:SONVPC>2.0.ZU;2-L
Abstract
The palladium-catalyzed cross-coupling of o-allylic and o-vinylic anil ides with vinylic halides and triflates produces substituted nitrogen heterocycles in good to high yields by a process involving vinylpallad ium addition to the olefin, rearrangement to a pi-allylpalladium inter mediate and subsequent intramolecular nucleophilic displacement of pal ladium. Different reactivity and regioselectivity in the palladium mig ration have been observed with different substituted alkenyl anilides. (C) 1998 Elsevier Science Ltd. All rights reserved.