Pd(II)-catalyzed dehydrogenative olefination of vinylic C-H bonds with allylic esters: general and selective access to linear 1,3-butadienes

Org Lett. 2012 Apr 6;14(7):1838-41. doi: 10.1021/ol300442w. Epub 2012 Mar 19.

Abstract

This work demonstrates a general and efficient method to prepare conjugated dienes by Pd(II)-catalyzed direct olefination of unactivated alkenes with allylic esters and acrylates via vinylic C-H activation. Various aryl and heteroaryl alkenes as well as aliphatic alkenes all give the desired linear 1,3-butadienes with retention of the traditional leaving groups such as OAc and other carboxylic acid ester groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Butadienes / chemical synthesis*
  • Butadienes / chemistry
  • Catalysis
  • Esters
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Alkenes
  • Butadienes
  • Esters
  • Palladium