Electrochemical sulfonylation of enamides with sodium sulfinates to access β-amidovinyl sulfones

• Published in: Organic & biomolecular chemistry Vol. 19; no. 38; pp. 8295 - 83
• Main Authors: Gu, Qingyun, Wang, Xin, Liu, Xinyi, Wu, Guixia, Xie, Yushan, Shao, Yu, Zhao, Yu, Zeng, Xiaobao
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 06.10.2021; Royal Society of Chemistry
• Subjects: Catalysis; Catalysts; Chemistry; Chemistry, Organic; Electrochemistry; Functional groups; Ions; Oxidants; Oxidizing agents; Physical Sciences; Science & Technology; Sodium; Sulfones; CATALYZED ASYMMETRIC HYDROGENATION; ELECTROSYNTHESIS; INSERTION; C(SP)-H ARYLSULFONYLATION; VINYL SULFONES; ALKYLATION; ACETYLAMINO ACRYLOSULFONES; C-H FUNCTIONALIZATION; ALKYNES; TRANSITION-METAL-FREE
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d1ob01485d

The electrochemical sulfonylation of enamides with sodium sulfinates was developed in an undivided cell in constant current mode, leading to the formation of β-amidovinyl sulfones in moderate to good yields. The catalyst-, electrolyte- and oxidant-free protocol features good functional group tolerance and employs electric current as a green oxidant. Mechanistic insights into the reaction indicate that the reaction may proceed via a radical mechanism. The electrochemical sulfonylation of enamides with sodium sulfinates in an undivided cell under catalyst- and exogenous redox reagent-free conditions was developed to access a variety of β-amidovinyl sulfones.