The rhodium-catalyzed mono-ortho C–H activation/carbenoid insertion/aldol-type cyclization of 3-aldehyde-2-phenyl-1H-indoles with diazo compounds has been developed.

In the past decades, CÀH oxidative olefination of indole at C-2, C-3, C-4 and C-7 positions was well addressed. We report here a rhodium-catalyzed NH-indole-directed ortho CÀH bond olefination of 2arylindoles. This cross-dehydrogenative-coupling proved to be broad in substrate scope, tolerating a variety of functional groups. The synthesis of 6H-isoindolo[2,1-a]indoles via rhodium-catalyzed ortho CÀH olefination and subsequent intramolecular aza-Michael reaction of 2-arylindoles was also demonstrated.

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