Enantiospecific Three-Component Alkylation of Furan and Indole

Mattia Silvi, Raffael Schrof, Adam Noble, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

16 Citations (Scopus)
278 Downloads (Pure)

Abstract

Furan- and indole-derived boronate complexes react with alkyl iodides under radical (photoredox) or polar (SN2) conditions to generate three-component alkylation products with high efficiency and complete stereospecificity. The methodology allows the incorporation of versatile functional groups such as nitriles, ketones, esters, sulfones, and amides, providing rapid access to complex chiral heteroaromatic molecules in enantioenriched form. Interestingly, while indolyl boronate complexes react directly with alkyl halides in a polar pathway, furyl boronates require photoredox catalysis. Careful mechanistic analysis revealed that the boronate complex not only serves as a substrate in the reaction but also acts as a reductive quencher for the excited state of the photocatalyst.

Original languageEnglish
Pages (from-to)4279-4282
Number of pages4
JournalChemistry - A European Journal
Volume24
Issue number17
Early online date28 Feb 2018
DOIs
Publication statusPublished - 20 Mar 2018

Keywords

  • Alkylation
  • Boron
  • Heterocycles
  • Metallate rearrangement
  • Photoredox catalysis

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