Catalytic (3 + 2) umpolung annulations of α-thioacyl carbenes with aryl isothiocyanates.

Chem Commun (Camb)

Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029, P. R. China.

Published: July 2022

1,2,3-Thiadiazoles serve as masked S-electrophilic thia-1,3-dipoles. Under rhodium/racemic BINAP catalysis, they undergo denitrogenative (3 + 2) umpolung transannulations with aryl isothiocyanates with inverse regioselectivity and excellent stereoselectivity, yielding -aryl 3-1,2-dithiol-()-3-imines in a redox-neutral, step-efficient, and functionality-tolerant manner. An intramolecular S-S bond is impressively forged.

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Source
http://dx.doi.org/10.1039/d2cc02882dDOI Listing

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