Asmic: An Exceptional Building Block for Isocyanide Alkylations

Org Lett. 2018 Sep 21;20(18):5910-5913. doi: 10.1021/acs.orglett.8b02574. Epub 2018 Sep 6.

Abstract

Asmic addresses the long-standing challenge of alkylating isocyanides, providing access to isocyanides with diverse substitution patterns. The o-anisylsulfanyl group serves a critical dual role by facilitating deprotonation-alkylation and providing a latent nucleophilic site through an unusual arylsulfanyl-lithium exchange.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / chemistry
  • Alkylation
  • Cyanides / chemistry*
  • Lithium / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Sulfhydryl Compounds / chemistry

Substances

  • Alkanes
  • Cyanides
  • Organometallic Compounds
  • Sulfhydryl Compounds
  • Lithium