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Enantiospecific Three-Component Alkylation of Furan and Indole

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Silvi Mattia, Schrof Raffael, Noble Adam, Aggarwal Varinder K.,
Project Merging Photoredox-Catalysis with 1,2-Boronate Rearrangements: Radical Introduction of Pentafluorosulfanyl and Trifluoromethyl Moieties
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Original article (peer-reviewed)

Journal Chemistry - A European Journal
Volume (Issue) 24(17)
Page(s) 4279 - 4282
Title of proceedings Chemistry - A European Journal
DOI 10.1002/chem.v24.17

Open Access

URL http://doi.org/10.1002/chem.v24.17
Type of Open Access Publisher (Gold Open Access)

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.
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