Nickel-Catalyzed Three-Component Cross-Electrophile Coupling of 1,3-Dienes with Aldehydes and Aryl Bromides

Org Lett. 2022 Jul 22;24(28):5023-5028. doi: 10.1021/acs.orglett.2c01648. Epub 2022 Jul 13.

Abstract

We herein report a Ni-catalyzed three-component cross-electrophile coupling of 1,3-dienes with aldehydes and aryl bromides using manganese metal as the reducing agent. This efficient protocol accomplishes dicarbofunctionalization of 1,3-dienes to synthesize diverse structural 1,4-disubstituted homoallylic alcohols by forming two new C-C bonds in one time. Mechanistic study suggests that an allyl-nickel(I) species is involved in the catalytic cycle.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes* / chemistry
  • Bromides
  • Catalysis
  • Molecular Structure
  • Nickel* / chemistry
  • Polyenes

Substances

  • Aldehydes
  • Bromides
  • Polyenes
  • Nickel