Chemoselective Dehydrogenation and Hetero-Arylation of Amides via Radical Translocation Enabled by Photoexcited Triplet Ketone Catalysis

We herein report the chemoselective dehydrogenation and heteroarylation of amides through photoexcited triplet ketone catalysis. Under mild reaction conditions, the generated aryl radical through the halogen atom transfer (XAT) process further undergoes an intramolecular 1,5-HAT event to generate an...

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Veröffentlicht in:Journal of organic chemistry 2024-11, Vol.89 (23), p.17818-17823
Hauptverfasser: Bisoyi, Akash, Behera, Amit, Tripathy, Alisha Rani, Simhadri, Vijay Kumar, Yatham, Veera Reddy
Format: Artikel
Sprache:eng
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Zusammenfassung:We herein report the chemoselective dehydrogenation and heteroarylation of amides through photoexcited triplet ketone catalysis. Under mild reaction conditions, the generated aryl radical through the halogen atom transfer (XAT) process further undergoes an intramolecular 1,5-HAT event to generate an α-amido alkyl radical, which then intercepted with either cobalt or a reduced cyano arene radical leads to dehydrogenated and heteroarylated products, respectively, in good yields.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02060