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Generation of Sulfonylated Tetrazoles through an Iron-Catalyzed Multicomponent Reaction Involving Sulfur Dioxide.

ABSTRACT: As a privileged motif, tetrazoles can be widely found in pharmaceuticals and materials science. Herein, a five-component reaction of cycloketone oxime esters, alkynes, DABCO·(SO₂)₂, and two molecules of trimethylsilyl azide under iron catalysis is developed, giving rise to a range of cyano-containing sulfonylated tetrazoles in moderate to good yields. This multicomponent reaction exhibits excellent selectivity and enables the formation of multiple new chemical bonds in one pot. A possible mechanism involving azidosulfonylation of alkynes, C-C bond cleavage of both cycloketone oxime esters and alkynes, and [3 + 2] cycloaddition of trimethylsilyl azide and the nitrilium cation intermediate is proposed. Additionally, the potential of terminal alkynes acting as powerful synthons for the synthesis of tetrazoles in a radical initiated process is demonstrated for the first time.

SUBMITTER: Zhang J

PROVIDER: S-EPMC7733023 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Generation of Sulfonylated Tetrazoles through an Iron-Catalyzed Multicomponent Reaction Involving Sulfur Dioxide.

Zhang Jun J Wang Xuefeng X Kuang Yunyan Y Wu Jie J

iScience 20201127 12

As a privileged motif, tetrazoles can be widely found in pharmaceuticals and materials science. Herein, a five-component reaction of cycloketone oxime esters, alkynes, DABCO·(SO2)2, and two molecules of trimethylsilyl azide under iron catalysis is developed, giving rise to a range of cyano-containing sulfonylated tetrazoles in moderate to good yields. This multicomponent reaction exhibits excellent selectivity and enables the formation of multiple new chemical bonds in one ...[more]

PMID: 33336165

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