Metal-free sulfonylation of arenes with <i>N</i>-fluorobenzenesulfonimide <i>via</i> cleavage of S-N bonds: expeditious synthesis of diarylsulfones.

Zhang, Xiaohui; Feng, Yueji; Tuo, Yanyan; Zheng, Qing-Zhong

Metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones.

Zhang, Xiaohui; Feng, Yueji; Tuo, Yanyan; Zheng, Qing-Zhong.

Afiliación

Zhang X; State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, National Demonstration Center for Experimental Chemistry Education, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, China. qzzheng@nxu.edu.cn.
Feng Y; State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, National Demonstration Center for Experimental Chemistry Education, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, China. qzzheng@nxu.edu.cn.
Tuo Y; State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, National Demonstration Center for Experimental Chemistry Education, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, China. qzzheng@nxu.edu.cn.
Zheng QZ; State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, National Demonstration Center for Experimental Chemistry Education, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, China. qzzheng@nxu.edu.cn.

Org Biomol Chem ; 20(4): 768-772, 2022 01 26.

Article en En | MEDLINE | ID: mdl-34989387

RESUMEN

A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., ß-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: China Pais de publicación: Reino Unido

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