A rhodium-catalyzed C-H amidation/cyclization sequence provides benzothiadiazine-1-oxides from sulfoximines and 1,4,2-dioxazol-5-ones in good yields. The reaction is characterized by a high functional group tolerance and, in contrast to most previous transformations of this type, is well-suited for alkyl--aryl-substituted sulfoximines.
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http://dx.doi.org/10.1021/acs.orglett.0c03212 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Anhui Normal University, School of Chemistry and Materials Science, 189 Jiuhua South Road, 241002, Wuhu, CHINA.
Achieving axially chiral biaryl dialdehydes through asymmetric catalysis remains significantly challenging due to the lack of efficient strategies. In this report, we developed a rhodium-catalyzed enantioselective C-H amidation through chiral transient directing group strategy. With this new approach, a series of axially chiral amido dialdehydes were achieved in up to 86% yields with 99.
View Article and Find Full Text PDFMolecules
January 2025
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
Efficient access to pyranoisoquinoline derivatives via rhodium-catalyzed double C-H functionalization of phenyl oxadiazoles and diazo compounds has been developed. Two C-C bonds and one C-O and C-N bond formation was realized by this tandem reaction, along with the formation of two heterocycles, affording diversified pyran-fused isoquinolines in moderate to good yields with broad functional group tolerance under mild reaction conditions.
View Article and Find Full Text PDFOrg Lett
January 2025
Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States.
General procedures for the rhodium-catalyzed annulation of aryl/heteroaryl -pivaloyl hydroxamic acids and norbornadiene have been developed. Employing norbornadiene as an acetylene equivalent enables utilization of diverse heterocyclic substrates for this transformation which fail to react or undergo competitive Lossen rearrangement under previously reported conditions. Microwave heating significantly reduces reaction times compared to conventional protocols and allows a one-step process to be realized.
View Article and Find Full Text PDFRSC Adv
December 2024
Natural and Medical Sciences Research Center (NMSRC), University of Nizwa Nizwa 616 Sulanate of Oman.
Diazo compounds are known to be good coupling partners in the synthesis of heterocycles, carbocycles and functionalized molecules a rhodium carbene-based strategy. Many heterocyclic and carbocyclic compounds, including isoquinolones and isocoumarins, quinoxalines, indoles, pyrrones, benzothazines, enaminones, benzenes and seven-membered rings, can be constructed using this rhodium-catalyzed system. The reaction mechanism involves C-H activation, carbene insertion and an annulation/functionalization sequence.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
Two routes to assemble the complete tricyclic core of alopecurone C are described. In the first-generation route, an efficient synthesis of the "eastern" half of the target, including a decagram-scale rhodium-catalyzed C-H insertion reaction, was developed. When this route proved intractable for assembling the final flavanone ring, a successful second-generation route was developed from a flavanone precursor (naringenin) employing a later stage C-H insertion.
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