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. 2016 Feb 5;18(3):356-9.
doi: 10.1021/acs.orglett.5b03185. Epub 2016 Jan 13.

Ruthenium Catalyzed Intramolecular C-S Coupling Reactions: Synthetic Scope and Mechanistic Insight

Shivani Sharma  1 , Ramdas S Pathare  1 , Antim K Maurya  1 , Kandasamy Gopal  1 , Tapta Kanchan Roy  1 , Devesh M Sawant  1 , Ram T Pardasani  1
Affiliations

Ruthenium Catalyzed Intramolecular C-S Coupling Reactions: Synthetic Scope and Mechanistic Insight

Shivani Sharma et al. Org Lett. .

Abstract

A ruthenium catalyzed intramolecular C-S coupling reaction of N-arylthioureas for the synthesis of 2-aminobenzothiazoles has been developed. Kinetic, isotope labeling, and computational studies reveal the involvement of an electrophilic ruthenation pathway instead of a direct C-H activation. Stereoelectronic effect of meta-substituents on the N-arylthiourea dictates the final regioselective outcome of the reaction.

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