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Auto-Tandem Catalysis: PdII -Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones.


ABSTRACT: A PdII 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.

SUBMITTER: Lamb CJC 

PROVIDER: S-EPMC5767738 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Auto-Tandem Catalysis: Pd<sup>II</sup> -Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones.

Lamb Claire J C CJC   Nderitu Bryan G BG   McMurdo Gemma G   Tobin John M JM   Vilela Filipe F   Lee Ai-Lan AL  

Chemistry (Weinheim an der Bergstrasse, Germany) 20171130 72


A Pd<sup>II</sup> 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 de  ...[more]

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