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Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates.

ABSTRACT: Catalysis using substoichiometric copper facilitates the synthesis of masked (hetero)aryl sulfinates under mild, base-free conditions from aryl iodides and the commercial sulfonylation reagent sodium 1-methyl 3-sulfinopropanoate (SMOPS). The development of a tert-butyl ester variant of the SMOPS reagent allowed the use of aryl bromide substrates. The sulfones thus generated can be unmasked and functionalized in situ to form a variety of sulfonyl-containing functional groups.

SUBMITTER: Merino MR

PROVIDER: S-EPMC11020165 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates.

Merino May R MR Cook Xinlan A F XAF Blakemore David C DC Moses Ian B IB Sach Neal W NW Shavnya Andre A Willis Michael C MC

Organic letters 20240108 14

Catalysis using substoichiometric copper facilitates the synthesis of masked (hetero)aryl sulfinates under mild, base-free conditions from aryl iodides and the commercial sulfonylation reagent sodium 1-methyl 3-sulfinopropanoate (SMOPS). The development of a tert-butyl ester variant of the SMOPS reagent allowed the use of aryl bromide substrates. The sulfones thus generated can be unmasked and functionalized in situ to form a variety of sulfonyl-containing functional groups. ...[more]

PMID: 38189248

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