Catalyst-Free Deaminative Functionalizations of Primary Amines via Photoinduced Single-Electron Transfer

Jingjing Wu, Phillip S. Grant, Xiabing Li, Adam Noble, Varinder K. Aggarwal*

*Corresponding author for this work

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

87 Citations (Scopus)
92 Downloads (Pure)

Abstract

The use of pyridinium‐activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst‐free conditions is described. By taking advantage of the visible‐light absorptivity of electron donor–acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et₃N, photoinduced single‐electron transfer could be initiated in the absence of a photocatalyst. This general reactivity platform has been applied to deaminative alkylations (Giese), allylations, vinylations, alkynylations, and thioetherifications. The mild conditions are amenable to a diverse range of primary and secondary alkyl pyridiniums and demonstrate broad functional group tolerance.
Original languageEnglish
Pages (from-to)5697-5701
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number17
DOIs
Publication statusPublished - 16 Apr 2019

Bibliographical note

© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

  • deamination
  • electron donor–acceptor complexes
  • Giese reactions
  • photochemistry
  • radical reactions

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