A Versatile Route to 2-Substituted Cyclic 1,3-Dienes via a Copper(I)-Catalyzed Cross-Coupling Reaction of Dienyl Triflates with Grignard Reagents
- 24 March 1998
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (8) , 2517-2522
- https://doi.org/10.1021/jo971737i
Abstract
A general synthesis of 2-substituted cyclic 1,3-dienes in two steps from α,β-unsaturated ketones has been developed. Formation of a dien-2-yl triflate followed by a copper(I)-catalyzed cross-coupling reaction with a Grignard reagent gives 2-substituted dienes in fair to excellent yields. Alkyl, aryl, and allyl Grignard reagents can be used.Keywords
This publication has 38 references indexed in Scilit:
- Platinacyclobutane chemistry: cis-disubstituted platinacyclobutane complex from bicyclo[4.1.0]heptaneOrganometallics, 1988
- Olefin synthesis via organometallic coupling reactions of enol triflatesAccounts of Chemical Research, 1988
- Electronic control of stereoselectivity. 9. The stereochemical course of electrophilic additions to aryl-substituted benzobicyclo[2.2.2]octadienesJournal of the American Chemical Society, 1981
- Analysis of organomagnesium and organolithium reagents using N-phenyl-1-naphthylamineThe Journal of Organic Chemistry, 1981
- Preparation of 2,3-Dialkylcyclohexa-1,3-dienes by the Bis-Wittig ReactionSynthesis, 1980
- Stoichiometric versus catalytic use of copper(I) salts in the synthetic use of main group organometallicsPublished by Walter de Gruyter GmbH ,1978
- Addition of chlorine to 1,3-butadiene with antimony pentachlorideThe Journal of Organic Chemistry, 1974
- Stereochemistry of polar 1,4-addition of bromine to dienes. Structure assignments for dibromocyclohexenes and dibromohexenesThe Journal of Organic Chemistry, 1973
- Vinyl‐Kationen, 12. Solvolyse von 1,3‐Cycloheptadien‐2‐yl‐und 1,3‐Cyclooctadien‐2‐yl‐trifluormethansulfonatEuropean Journal of Inorganic Chemistry, 1973
- PhenylcyclohexadienesThe Journal of Organic Chemistry, 1968