A Photocatalytic Regioselective Hydroaminoalkylation of Aryl-Substituted Alkenes with Simple Amines

02 April 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A photocatalytic method for the alpha-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of alpha-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the alpha-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the beta-position. Simple scale-up is demonstrated under continuous-flow conditions, highlighting the practicality of the method.

Keywords

photoredox
Visible light photocatalysis
α-aminoalkyl radical
electron-deficient alkenes
β-amino acid
styrene
DFT
continuous flow
anti-Markovnikov
anti-Giese

Supplementary materials

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Larionova - Supporting Information
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