Auto-Tandem Catalysis: Pd(II)-Catalysed Dehydrogenation/Oxidative Heck of Cyclopentane-1,3-diones

Claire J C Lamb, Bryan G Nderitu, Gemma McMurdo, John MTobin, Filipe Vilela, and Ai-Lan Lee

• Institute of Chemical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, United Kingdom

A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a one-pot procedure: dehydrogenation of 2,2-disubstituted cyclopentane-1,3-diones and
the subsequent oxidative Heck coupling. This auto-tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenation/oxidative Heck in flow. In addition, a telescoped reaction involving enantioselective desymmetrisation of the all-C quaternary centre was successfully achieved.

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