Organic Chemistry

A phenyl ring hops with a light step

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Science  18 Aug 2017:
Vol. 357, Issue 6352, pp. 657-658
DOI: 10.1126/science.357.6352.657-b

It is generally rather difficult to break bonds connecting alkyl and aryl carbons. Shu et al. show that blue light and a nearby nitrogen can smooth the way. Specifically, they use a base and a light-activated iridium catalyst to deprotonate and oxidize a γ-diarylamine. The nitrogen can then reach around and swipe one of the aryl rings, which can be replaced by hydrogen, bromine, or a carbon center in a variety of Michael acceptors. The reaction proceeds at room temperature when irradiated by light-emitting diodes.

Angew. Chem. Int. Ed. 10.1002/anie.201704068 (2017).

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