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Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.

ABSTRACT: A silver-catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN₃ is reported. This three-component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of ?-sulfonyl enamines without electron-withdrawing groups on the nitrogen atom. These enamines are found to be suitable for a variety of further transformations.

SUBMITTER: Ning Y

PROVIDER: S-EPMC5655761 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.

Ning Yongquan Y Ji Qinghe Q Liao Peiqiu P Anderson Edward A EA Bi Xihe X

Angewandte Chemie (International ed. in English) 20170707 44

A silver-catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN<sub>3</sub> is reported. This three-component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of β-sulfonyl enamines without electron-withdrawing groups on the nitrogen atom. These enamines are found to be suitable for a variety of furthe ...[more]

PMID: 28627090

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