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Visible-Light-Mediated Synthesis of 1,2,4-Dithiazolidines from β-Ketothioamides through a Hydrogen-Atom-Transfer Photocatalytic Approach of Eosin Y

2019; American Chemical Society; Volume: 84; Issue: 9 Linguagem: Inglês

10.1021/acs.joc.9b00406

1520-6904

Monish Arbaz Ansari, Dhananjay Yadav, Sonam Soni, Abhijeet Srivastava, Maya Shankar Singh,

Catalytic C–H Functionalization Methods

An efficient protocol for visible-light-mediated synthesis of a specific class of 1,2,4-dithiazolidines from β-ketothioamides is devised employing eosin Y as a photoinitiator at ambient temperature in an open pot. The reaction proceeds via an in situ-generated thiyl radical followed by dimerization/deaminative cyclization cascade, enabling the creation of a dithiazolidine ring through successive formation of S–S and N–C bonds under metal- and additive-free conditions. Remarkably, the benign conditions, sustainability, and quantifying forbearance of wide horizons of functional groups are added characteristics to the strategy. The developed hydrogen-atom-transfer methodology will be helpful in postsynthetic modification via added synthetic handles.