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Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access allenes and dienes.

ABSTRACT: The radical-mediated difunctionalization of 1,3-enynes facilitates rapid access to structurally diverse allenes and dienes. Whereas, owing to the existence of multiple active sites in conjugated 1,3-enynes, regulating selectivity in difunctionalized addition via a single transition-metal-catalyzed radical tandem process remains elusive. Herein, we disclose an intriguing protocol of substrate-controlled nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes with the assistance of sulfonyl chlorides and arylboronic acids. This valuable synthetic utility respectively delivers a series of highly functionalized and synthetically challenging allenyl sulfones and dienyl sulfones from fine-tuned 1,3-enynes by one step, which provides a facile approach for complex sulfone-containing drug molecules synthesis.

SUBMITTER: Chi Z

PROVIDER: S-EPMC11339949 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access allenes and dienes.

Chi Zhuomin Z Zhou Yongchao Y Liu Bingbing B Xu Xiaojing X Liu Xueyuan X Liang Yongmin Y

Chemical science 20240723 33

The radical-mediated difunctionalization of 1,3-enynes facilitates rapid access to structurally diverse allenes and dienes. Whereas, owing to the existence of multiple active sites in conjugated 1,3-enynes, regulating selectivity in difunctionalized addition <i>via</i> a single transition-metal-catalyzed radical tandem process remains elusive. Herein, we disclose an intriguing protocol of substrate-controlled nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes with the assistance of ...[more]

PMID: 39183907

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