Bicatalytic Allylation–Cross-Metathesis Reactions as γ-Carbonyl Cation Equivalents

Authors

Jake R. Henkie
Sugadar Dhaliwal
James R. Green, University of WindsorFollow

Document Type

Article

Publication Date

10-2012

Publication Title

Synlett

Volume

23

Issue

16

First Page

2371

Keywords

allylation, electrophilic aromatic substitution, indium, metathesis, umpolung

Last Page

2371

Abstract

The products corresponding to the reactions of arenes and γ-carbonyl cations may be obtained by a one-pot, bicatalytic process involving InCl₃-catalyzed arene allylation and cross metathesis with electron-deficient alkenes. The process is successful with electronically neutral and electron-rich arenes, and modestly Lewis basic donor groups are tolerated with an increase in InCl₃ loading from 10 mol% to 15 mol%, and in one case, 20 mol%.

DOI

10.1055/s-0032-1317045

Funding Reference Number

NSERC

Comments

First published in Synlett, copyright © Georg Thieme Verlag, an imprint of Thieme Publishing. To access the final version, see DOI: 10.1055/s-0032-1317045 at https://www.thieme-connect.com/products/ejournals/html/10.1055/s-0032-1317045.

Recommended Citation

Henkie, Jake R.; Dhaliwal, Sugadar; and Green, James R.. (2012). Bicatalytic Allylation–Cross-Metathesis Reactions as γ-Carbonyl Cation Equivalents. Synlett, 23 (16), 2371-2371.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/67