Regioselective Addition of Sulfur and Amine Nucleophiles To Assemble S═C-S, S-N, and Umpolung C-N Bonds: Exploration of the -CBr3 Group as a Synthetic Equivalent of S═C-S

Ankush Gupta; Guddeangadi N Gururaja

doi:10.1021/acs.orglett.4c00157

Regioselective Addition of Sulfur and Amine Nucleophiles To Assemble S═C-S, S-N, and Umpolung C-N Bonds: Exploration of the -CBr₃ Group as a Synthetic Equivalent of S═C-S

Org Lett. 2024 Mar 8;26(9):1874-1879. doi: 10.1021/acs.orglett.4c00157. Epub 2024 Feb 27.

Authors

Ankush Gupta¹, Guddeangadi N Gururaja¹

Affiliation

¹ School of Chemical Sciences, Central University of Gujarat, Gandhinagar, Gujarat 382030, India.

PMID: 38411402
DOI: 10.1021/acs.orglett.4c00157

Abstract

The regioselective addition of sulfur and amine nucleophiles to a -CBr₃ unit and nitromethyl moiety in a molecule with the installation of a five-diverse bond structure to novel isothiazole-5(2H)-thione is demonstrated. Umpolung of the nitromethyl group leads to a novel scaffold with selective C-N bond formation. Consequently, differentiating reactive centers by sulfur and amine nucleophiles has been proposed to create unique S-N bonds in conjunction with the dithioate (S═C-S-) moiety. This protocol allows for exploration of the -CBr₃ moiety as a synthetic equivalent of the dithioate (S═C-S-) unit during the reaction.