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A novel rhodium(III)-catalyzed amide carbonyl group directed alkenylation reaction between oxindoles and alkenes has been reported, which provides an efficient method for the synthesis of valuable and versatile functionalized N-(2E,4Z)-butadiene substituted oxindole derivatives. Oxindoles as novel directing groups have been well applied in this paper.

An efficient rhodium(III)-catalyzed C–H activation has been developed by using 7-azaindole as a directing group. A wide variety of olefinated 7-azaindole derivatives and N-naphthylazole derivatives have been selectively formed in moderate to excellent yields when alkenes or alkynes act as the C–H coupling partner.

A novel one-pot synthesis of π-conjugated polycyclic compounds, which could undergo further facile transformation to form complex polycyclic heteroarene compounds, has been realized between 7-azaindoles and α,β-unsaturated ketones. This distinctive cascade process proceeds via a rhodium(iii)-catalyzed alkylation/copper-catalyzed radical annulation-aromatization pathway.

A convenient rhodium(III)-catalyzed cascade reaction of 7-azaindoles and alkynes through multiple C-H bond activation for the synthesis of unique [5]azahelicenes has been developed. The optical property of these screw-shaped helicene derivatives could be further utilized in electronic devices to recognize mercury ions.

An efficient rhodium-catalyzed dehydrogenative Heck-type reaction between N-aryl-substituted 7-azaindoles and various alkenes through a H2-releasing process without the need of any oxidizing agent was developed. The novel methodology broadens the scope of metal-catalyzed hydrogen-releasing reactions to include rhodium catalysis.