Efficient Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer

02 June 2020, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the
development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism, key to circumvent
the problems associated with the low electron affinity of alkenes, is supported by experimental and computational studies. The reaction is applied
to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing
substituents in the aromatic ring and with good functional group compatibility.

Keywords

Photoredox Catalysts
Hydrogen Atom Transfer
Hantzsch ester
Transfer Hydrogenation
Photocatalysis

Supplementary materials

Title
Description
Actions
Title
HAT reduction QMUL - ESI
Description
Actions

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