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Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones.

ABSTRACT: An efficient Ni(ClO₄)₂·6H₂O-promoted amidoalkylation reaction for the synthesis of 3-substituted isoindolinones involving various γ-hydroxy lactams and nucleophiles has been successfully developed. The transformation proceeds with both carbon (ketones and arenes) and heteroatom (alcohols, thiols, and amines) nucleophiles and in both intermolecular and intramolecular manners. The prominent features of the present strategy are wide substrate scope, excellent group tolerability, and moderate to good yields (up to 96% yield). The present strategy is also characterized by remarkable superiority over the current synthetic methods. Furthermore, the reaction could be scaled up to the multigram scale.

SUBMITTER: Zhang S

PROVIDER: S-EPMC6868882 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones.

Zhang Shuo S Shi Xinhua X Li Jichao J Hou Zitong Z Song Zihe Z Su Xiaofeng X Peng Dan D Wang Feng F Yu Yitao Y Zhao Guilong G

ACS omega 20191105 21

An efficient Ni(ClO4)2·6H2O-promoted amidoalkylation reaction for the synthesis of 3-substituted isoindolinones involving various γ-hydroxy lactams and nucleophiles has been successfully developed. The transformation proceeds with both carbon (ketones and arenes) and heteroatom (alcohols, thiols, and amines) nucleophiles and in both intermolecular and intramolecular manners. The prominent features of the present strategy are wide substrate scope, excellent group ...[more]

PMID: 31763566

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