Palladium-Catalyzed Stereo- and Regiospecific Allylation of Aryl Halides with Homoallyl Alcohols via Retro-Allylation: Selective Generation and Use of σ-Allylpalladium
- 26 January 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (7), 2210-2211
- https://doi.org/10.1021/ja058055u
Abstract
Treatment of tertiary homoallyl alcohol with aryl halide under palladium catalysis resulted in the transfer of the allyl moiety of the homoallyl alcohol to aryl halide and yielded the corresponding cross-coupling product stereo- and regiospecifically. The transfer process includes retro-allylation, which proceeds via a conformationally regulated six-membered transition state. The retro-allylation can be regarded as a method for the stereo- and regiospecific preparation of σ-allylpalladium.Keywords
This publication has 4 references indexed in Scilit:
- Innovative reactions mediated by zirconoceneThe Chemical Record, 2004
- Reaction of second-row transition-metal atoms with methaneJournal of the American Chemical Society, 1991
- A triply convergent total synthesis of l(-)-prostaglandin E2Journal of the American Chemical Society, 1981
- Nucleophilic and organometallic displacement reactions of allylic compounds: stereo-and regiochemistryTetrahedron, 1980