General and facile method for exo-methlyene synthesis via regioselective C-C double-bond formation using a copper-amine catalyst system

Org Lett. 2014 Nov 7;16(21):5816-9. doi: 10.1021/ol502953w. Epub 2014 Oct 15.

Abstract

In this study, for distal-selective β-hydride elimination to produce exomethylene compounds with a newly formed Csp(3)-Csp(3) bond between tertiary alkyl halides and α-alkylated styrenes, a combination of a Cu(I) salt and a pyridine-based amine ligand (TPMA) is found to be a very efficient catalyst system. The yields and regioselectivities were high, and the regioselectivity was found to be dependent on the structure of the alkyl halide, with bulky alkyl halides showing the highest distal selectivities.