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

Author:
Sharma, Shivani, Pathare, Ramdas S., Maurya, Antim K., Gopal, Kandasamy, Roy, Tapta Kanchan, Sawant, Devesh M., Pardasani, Ram T.
Source:
Organic letters 2016 v.18 no.3 pp. 356-359
ISSN:
1523-7052
Subject:
Lewis acids, carbon-hydrogen bond activation, chemical reactions, chemical structure, isotope labeling, organic compounds, regioselectivity, ruthenium
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.
Agid:
5792260