Herein, we report acid-mediated divergent annulations of (-aryl)-alkynyl sulfonamides. The substituent at the position of the -aryl group determines two diverse reaction paths, leading to the selective assembly of benzo-fused sultams and spirocyclic sultams. This strategy provides a series of benzo/spiro-sultams with wide functional group compatibility and good to excellent yields under mild reaction conditions. Additionally, scale-up reaction and further transformations of the products were also carried out to demonstrate the utility of the protocol.

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http://dx.doi.org/10.1021/acs.joc.4c01517DOI Listing

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Herein, we report acid-mediated divergent annulations of (-aryl)-alkynyl sulfonamides. The substituent at the position of the -aryl group determines two diverse reaction paths, leading to the selective assembly of benzo-fused sultams and spirocyclic sultams. This strategy provides a series of benzo/spiro-sultams with wide functional group compatibility and good to excellent yields under mild reaction conditions.

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School of Chemistry, Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, and Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, Sun Yat-Sen University, Guangzhou, 510006, P. R. China.

Given the tremendous success of (p-cymene)Ru-catalyzed C-H activation over the past 20 years, the community has long been aware that the development of chiral η-benzene (Ben) ligands should be a potent strategy for achieving the attractive but incredibly underdeveloped ruthenium(II)-catalyzed asymmetric C-H activation. However, it has rarely been achieved due to the severe difficulty in developing proper chiral Ben ligands. In particular, designing chiral Ben ligands by connecting a benzene fragment to a chiral framework including benzene rings remained an unsolved challenge until this effort.

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