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Photo-induced imino functionalizations of alkenes via intermolecular charge transfer.

ABSTRACT: A catalyst-free photosensitized strategy has been developed for regioselective imino functionalizations of alkenes via the formation of an EDA complex. This photo-induced protocol facilitates the construction of structurally diverse β-imino sulfones and vinyl sulfones in moderate to high yields. Mechanistic studies reveal that the reaction is initiated with an intermolecular charge transfer between oximes and sulfinates, followed by fragmentation to generate a persistent iminyl radical and transient sulfonyl radical. This catalyst-free protocol also features excellent regioselectivity, broad functional group tolerance and mild reaction conditions. The late stage functionalization of natural product derived compounds and total synthesis of some bioactive molecules have been demonstrated to highlight the utility of this protocol. Meanwhile, the compatibility of different donors has proved the generality of this strategy.

SUBMITTER: Zhang XX

PROVIDER: S-EPMC10583702 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Photo-induced imino functionalizations of alkenes <i>via</i> intermolecular charge transfer.

Zhang Xiang-Xin XX Zheng Hao H Mei Yong-Kang YK Liu Yan Y Liu Ying-Ying YY Ji Ding-Wei DW Wan Boshun B Chen Qing-An QA

Chemical science 20230925 40

A catalyst-free photosensitized strategy has been developed for regioselective imino functionalizations of alkenes <i>via</i> the formation of an EDA complex. This photo-induced protocol facilitates the construction of structurally diverse β-imino sulfones and vinyl sulfones in moderate to high yields. Mechanistic studies reveal that the reaction is initiated with an intermolecular charge transfer between oximes and sulfinates, followed by fragmentation to generate a persistent iminyl radical an ...[more]

PMID: 37860665

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