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Synthesis 2024; 56(11): 1702-1710
DOI: 10.1055/s-0043-1763660
DOI: 10.1055/s-0043-1763660
paper
New Trends in Organic Synthesis from Chinese Chemists
Photoredox-Catalyzed C(sp3)–H Difluoroallylation of Amides
The authors are grateful for financial support provided by the National Key R&D Program of China (2021YFA1502500), National Natural Science Foundation of China (22071203), and Fundamental Research Funds for the Central Universities (20720210014).
Abstract
A photoredox-catalyzed, bromine-radical-mediated C(sp3)–H difluoroallylation of amides is disclosed. This modular approach exploits the hydrogen atom transfer (HAT) ability of photooxidatively generated bromine radicals to convert both cyclic and acyclic amides into the corresponding α-amino alkyl radicals that then are coupled with readily available trifluoromethyl alkenes. This method is distinguished by its mild conditions, broad substrate scope (30 examples), and the use of a simple HAT reagent, namely sodium bromide (NaBr). This strategy offers a promising paradigm for the incorporation of carbonyl isosteres into saturated aliphatic amines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1763660.
- Supporting Information
Publication History
Received: 10 October 2023
Accepted after revision: 27 November 2023
Article published online:
03 January 2024
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