Remarkably reactive dihydroindoloindoles via palladium-catalysed dearomatisation.

Palladium-catalysed dearomatisation reactions allow access to a previously unknown class of indoloindole heterocycle: 5,10b-dihydroindolo[2,3-b]indoles. The highly reactive nature of these compounds is demonstrated by their facile reactions with water and with hydride, alkyl, aryl and allyl-based organometallic nucleophiles.

Reactive 4a-alkyl-4aH-carbazoles by catalytic dearomatisation, and their unusual dimerisation and dealkylation reactions.

Despite their intrinsic instability, 4a-alkyl-4aH-carbazoles can be generated by a catalytic dearomatisation process; their reactivity is demonstrated by facile dealkylation and highly unusual cyclodimerisation processes.