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Li, Qing‐Zhu; Zeng, Rong; Fan, Yang; Liu, Yan‐Qing; Qi, Ting; Zhang, Xiang; Li, Jun‐Long
Angewandte Chemie International Edition, April 4, 2022, Letnik: 61, Številka: 15Journal Article
The direct functionalization of inert C(sp3)−H bonds under environmentally benign catalytic conditions remains a challenging task in synthetic chemistry. Here, we report an organocatalytic remote C(sp3)−H acylation of amides and cascade cyclization through a radical‐mediated 1,5‐hydrogen atom transfer mechanism using N‐heterocyclic carbene as the catalyst. Notably, a diversity of nitrogen‐containing substrates, including simple linear aliphatic carbamates and ortho‐alkyl benzamides, can be successfully applied to this organocatalytic system. With the established protocol, over 120 examples of functionalized δ‐amino ketones and isoquinolinones with diverse substituents were easily synthesized in up to 99 % yield under mild conditions. The robustness and generality of the organocatalytic strategy were further highlighted by the successful acylation of unactivated C(sp3)−H bonds and late‐stage modification of pharmaceutical molecules. Then, the asymmetric control of the radical reaction was attempted and proven feasible by using a newly designed chiral thiazolium catalyst, and moderate enantioselectivity was obtained at the current stage. Preliminary mechanistic investigations including several control reactions, KIE experiments, and computational studies shed light on the organocatalytic radical reaction mechanism. An N‐heterocyclic carbene catalyzed remote C(sp3)−H acylation of amides was developed, and also combined with a cascade cyclization. Over 120 functionalized δ‐amino ketones and isoquinolinones with diverse substituents were synthesized in up to 99 % yield under mild conditions. Preliminary mechanistic investigations shed light on the organocatalytic radical reaction mechanism.
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