Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions†
Ying Cheng
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Carsten Bolm
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany)
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany)Search for more papers by this authorYing Cheng
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Carsten Bolm
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany)
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany)Search for more papers by this authorY.C. thanks the China Scholarship Council for a pre-doctoral stipend.
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.
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