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Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide.

ABSTRACT: A metal- and base-free 5-endo-trig sulfonylative cyclization between 1,5-dienes, aryldiazonium salts and SO₂ (from SOgen) is presented. This method could successfully produce sulfonylated pyrrolin-2-ones in one pot with excellent regioselectivity and good-to-excellent yields. This strategy features mild reaction conditions and broad substrate scope. Moreover, a scale-up reaction and three synthetic applications demonstrate the practicality of this method. Lastly, control experiments indicate that the 5-endo-trig sulfonylative cyclization may proceed in a radical pathway.

SUBMITTER: Wang X

PROVIDER: S-EPMC9170380 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide.

Wang Xiaohong X You Fengzhi F Xiong Baojian B Chen Lei L Zhang Xuemei X Lian Zhong Z

RSC advances 20220606 26

A metal- and base-free 5-endo-trig sulfonylative cyclization between 1,5-dienes, aryldiazonium salts and SO2 (from SOgen) is presented. This method could successfully produce sulfonylated pyrrolin-2-ones in one pot with excellent regioselectivity and good-to-excellent yields. This strategy features mild reaction conditions and broad substrate scope. Moreover, a scale-up reaction and three synthetic applications demonstrate the practicality of this method. Lastly, control experi ...[more]

PMID: 35754872

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