Photocatalytic Umpolung of - and -substituted Alkenes for the Synthesis of 1,2-amino Alcohols and Diols

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 7

PMID 34094368

Citations 8

Authors

Stephanie G E Amos

Stefano Nicolai

Jerome Waser

Affiliations

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Abstract

We report an organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolung of the innate reactivity of the alkenes, enabling addition of a nucleophilic benzoate followed by radical alkynylation.

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