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Ir-Catalyzed C-H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group
Yun-Fei Zhang1, Bin Wu1, Zhang-Jie Shi1,2
1Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871, P.R. China.
Abstract:
Ir-catalyzed sp2 C-H amidation of aldehydes with various anilines as stoichiometric or catalytic directing groups was accomplished. A wide range of substrates were selectively amidated in good to excellent yields with broad functional group tolerance. The iridacycle complexes were isolated, characterized, and proved as key intermediates. Kinetic studies and Hammett plots provided detailed understandings of this amidation. According to the mechanism, the electron-rich ArSO2 N3 was proved effective for intermolecular sp3 C-H amidation.
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