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Dess-Martin Periodinane-Mediated Oxidative Coupling Reaction of Isoquinoline with Benzyl Bromide.

ABSTRACT: Dess-Martin periodinane (DMP) is a broadly applicable oxidant in chemical synthesis. In this work, an efficient and convenient synthesis of N-substituted isoquinolinone derivatives mediated by DMP was achieved through the oxidative coupling reaction of functionalized isoquinoline with readily available benzyl bromide, which is a metal-free, mild, and practical method for synthesizing isoquinoline-1,3-dione or isoquinoline-1,3,4-trione derivatives in excellent yields. The H₂O¹⁸-labeling experiment was performed to gain insight into the possible mechanism for this reaction.

SUBMITTER: Yang C

PROVIDER: S-EPMC9919522 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Dess-Martin Periodinane-Mediated Oxidative Coupling Reaction of Isoquinoline with Benzyl Bromide.

Yang Chunmei C Zhang Guoqing G Tang Senling S Pan Yang Y Shao Huawu H Jiao Wei W

Molecules (Basel, Switzerland) 20230117 3

Dess-Martin periodinane (DMP) is a broadly applicable oxidant in chemical synthesis. In this work, an efficient and convenient synthesis of <i>N</i>-substituted isoquinolinone derivatives mediated by DMP was achieved through the oxidative coupling reaction of functionalized isoquinoline with readily available benzyl bromide, which is a metal-free, mild, and practical method for synthesizing isoquinoline-1,3-dione or isoquinoline-1,3,4-trione derivatives in excellent yields. The H<sub>2</sub>O<su ...[more]

PMID: 36770590

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