Photoinduced Nitrogen-to-Alkyl Radical Relay Heck Reaction of o‑Alkylbenzamides with Vinyl Arenes by Palladium Catalysis

Here, a palladium-catalyzed photoinduced N-to-alkyl radical relay Heck reaction of o-alkylbenzamides at benzylic sites with vinyl arenes is described. The reaction employs neither exogeneous photosensitizers nor external oxidants. It is proposed to proceed via a N-to-alkyl hybrid palladium–radical m...

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Bibliographic Details
Published in:Organic letters 2023-05, Vol.25 (20), p.3664-3669
Main Authors: Sheng, Xia-xin, Du, Yu-jia, Li, Jun-hua, Teng, Qiao-qiao, Chen, Ming
Format: Article
Language:English
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Summary:Here, a palladium-catalyzed photoinduced N-to-alkyl radical relay Heck reaction of o-alkylbenzamides at benzylic sites with vinyl arenes is described. The reaction employs neither exogeneous photosensitizers nor external oxidants. It is proposed to proceed via a N-to-alkyl hybrid palladium–radical mechanism which occurs under mild conditions that are compatible with a wide range of functional groups. The products are easily transformed to azepinone derivatives, which are prevalent in pharmaceuticals and natural products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01030