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Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.

ABSTRACT: 1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal catalysts, specialized or air-sensitive ligands, high temperatures, and disulfides (R2 S2 ). Herein, a general and efficient strategy utilizing ethynylbenziodoxolone (EBX) reagents and thiols is presented that results in the formation of 1,2-dithio-1-alkenes with excellent regioselectivity and stereoselectivity through unprecedented reactivity between the EBX and the thiol. This operationally simple procedure utilizes mild conditions, which result in a broad substrate scope and high functional-group tolerance. The observed unexpected reactivity has been rationalized through both experimental results and DFT calculations.

SUBMITTER: Liu B

PROVIDER: S-EPMC7044075 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.

Liu Bin B Alegre-Requena Juan V JV Paton Robert S RS Miyake Garret M GM

Chemistry (Weinheim an der Bergstrasse, Germany) 20200122 11

1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal catalysts, specialized or air-sensitive ligands, high temperatures, and disulfides (R<sub>2</sub> S<sub>2</sub> ). Herein, a general and efficient strategy utilizing ethynylbenziodoxolone (EBX) reagents and thiols is presented that results in t ...[more]

PMID: 31657063

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