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An efficient rhodium(III)-catalyzed vinylic sp2 C–H bond activation of 7-azaindoles with alkynes is reported, leading to the controlled synthesis of stereodefined diene and fused polycyclic heteroarene products. The novel strategy for the synthesis of diverse coupling products was controlled by the reaction conditions and the substitutions on the vinyl group.

A highly efficient Ir(III)-catalyzed cascade cyclization of indoles and diazoes giving access to unique pentacyclic fused carbazoles has been developed. This novel strategy expanded the application scope of coupling partners to take diazo compounds as a C2 source, and two new cycles, three new C-C and one new C-N bonds were formed in one-pot.

Rhodium-catalyzed tandem annulation reactions via olefination and subsequent intramolecular C-Michael-type cyclization represent an efficient approach for the direct construction of CC bonds. The simple and atom-economic strategy produces various alkylation derivatives of 7-azaindole with a quaternary carbon center from 7-azaindoles and olefins.

Tetracyclic products are efficiently obtained by application of a base as key of the annulation reactions.

Various 1-aryl-1H-pyrrolo[2,3-b]pyridines are selectively coupled with styrene, acrylic acid derivatives or vinyl ethyl ether in position 2 of the aryl substituent.

Various rhodium-catalyzed double C–H activations are reviewed. These powerful strategies have been developed to construct C–C bonds, which might be widely embedded in complex aza-fused heterocycles, polycyclic skeletons and heterocyclic scaffolds. In particular, rhodium(III) catalysis shows good selectivity and reactivity to functionalize the C–H bond, generating reactive organometallic intermediates in most of the coupling reactions. Generally, intermolecular, intramolecular and multi-component coupling reactions via double C–H activations with or without heteroatom-assisted chelation are discussed in this review.

Ruthenium(II)-catalyzed oxidative coupling of NH protic amides with alkynes has been developed for the synthesis of a diversity of complex structures, such as N-acyl indole and tricyclic amide derivatives.

Rhodium(III)-catalyzed double C–H activation involving N-directed ortho C–H activation and subsequent roll-over C–H activation of the heterocycle ring has been developed to form complex 7-azaindole derivatives in moderate to excellent yields. A broad scope of 7-azaindoles and internal alkynes has been demonstrated in this oxidative annulation reaction.

The novel C—H activation methodology exhibits a broad substrate scope with respect to the indole/pyrrole and ketone educts.

A chiral Lewis base organocatalyzed asymmetric hydrosilylation of α-substituted β-enamino esters is presented. The reactions proceeded through dynamic kinetic resolution to afford various enantioenriched β2-amino esters with high yields (up to 98%) in moderate enantioselectivities (up to 77% ee).

This efficient title reaction affords the corresponding 3,3 disubstituted oxindole derivatives in moderate to good yields and with up to 96% enantiomeric excess.