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Cationic Ir(I)-Catalyzed sp3 C−H Bond Alkenylation of Amides with Alkynes

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journal contribution
posted on 16.04.2009, 00:00 by Kyoji Tsuchikama, Mitsugu Kasagawa, Kohei Endo, Takanori Shibata
A cationic Ir(I)-BINAP catalyst cleaved sp3 C−H bonds of arylamides rather than sp2 C−H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp3 C−H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.