A cationic Ir(I)-BINAP catalyst cleaved sp(3) C-H bonds of arylamides rather than sp(2) 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 sp(3) C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.
Secondary sp 3 C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.
The cationic iridium complex ([Ir(cod) 2 ]OTf + rac-BINAP) efficiently catalyzed a sequential process of ortho-C-H bond functionalization, cyclization and dehydration, leading to a concise preparation of 1-methylene indene (benzofulvene) derivatives. The iridium complex operated as a catalyst in the ortho-C-H bond alkenylation of aryl ketones with alkynes and as a Lewis acid catalyst in the cyclization of the alkenylated product and the subsequent dehydration.
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