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Regioselective Syntheses of 1,2‐Benzothiazines by Rhodium‐Catalyzed Annulation Reactions
Author(s) -
Cheng Ying,
Bolm Carsten
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501583
Subject(s) - regioselectivity , rhodium , annulation , carbene , catalysis , chemistry , domino , aryl , functional group , biphenyl , combinatorial chemistry , organic chemistry , medicinal chemistry , alkyl , polymer
Abstract Rhodium‐catalyzed directed carbene insertions into aromatic CH 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.