Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions

Rhodium‐catalyzed directed carbene insertions into aromatic CH bonds of S‐aryl sulfoximines lead to intermediates, which upon dehydration provide 1,2‐benzothiazines in excellent yields. The domino‐type process is regioselective and shows a high functional‐group tolerance. It is scalable, and the on...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-10, Vol.54 (42), p.12349-12352
Main Authors: Cheng, Ying, Bolm, Carsten
Format: Article
Language:English
Subjects:
Byproducts
Carbenes
Catalysis
Chemical reactions
CH activation
Dehydration
diazo compounds
heterocycles
Insertion
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
rhodium
Rhodium - chemistry
Stereoisomerism
Thiazines - chemical synthesis
Thiazines - chemistry
Tolerances
Transformations
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Summary:Rhodium‐catalyzed directed carbene insertions into aromatic CH bonds of S‐aryl sulfoximines lead to intermediates, which upon dehydration provide 1,2‐benzothiazines in excellent yields. The domino‐type process is regioselective and shows a high functional‐group tolerance. It is scalable, and the only by‐products are dinitrogen and water. Three illustrative transformations underscore the synthetic value of the products. Domino effect: Rhodium‐catalyzed annulation reactions provide 1,2‐benzothiazines in excellent yields starting from S‐aryl sulfoximines and diazo compounds. The catalysis shows a high functional‐group tolerance and the process demonstrates excellent regioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201501583