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

Claire J. C. Lamb; Bryan G. Nderitu; Gemma McMurdo; John M. Tobin; Filipe Vilela; Ai-Lan Lee

doi:10.1002/chem.201704442

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

Claire J. C. Lamb, Bryan G. Nderitu, Gemma McMurdo, John M. Tobin, Filipe Vilela, Ai-Lan Lee

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Abstract

A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a onepot 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.

Original language	English
Pages (from-to)	18282–18288
Number of pages	7
Journal	Chemistry - A European Journal
Volume	23
Issue number	72
Early online date	30 Nov 2017
DOIs	https://doi.org/10.1002/chem.201704442
Publication status	Published - 22 Dec 2017

Keywords

aerobic oxidation
oxidative Heck
palladium
auto-tandem catalysis
one-pot synthesis

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Cite this

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

abstract = "A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a onepot 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.",

keywords = "aerobic oxidation, oxidative Heck , palladium, auto-tandem catalysis , one-pot synthesis ",

author = "Lamb, {Claire J. C.} and Nderitu, {Bryan G.} and Gemma McMurdo and Tobin, {John M.} and Filipe Vilela and Ai-Lan Lee",

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T1 - Auto-Tandem Catalysis: PdII-Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones

AU - Lamb, Claire J. C.

AU - Nderitu, Bryan G.

AU - McMurdo, Gemma

AU - Tobin, John M.

AU - Vilela, Filipe

AU - Lee, Ai-Lan

PY - 2017/12/22

Y1 - 2017/12/22

N2 - A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a onepot 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.

AB - A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a onepot 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.

KW - aerobic oxidation

KW - oxidative Heck

KW - palladium

KW - auto-tandem catalysis

KW - one-pot synthesis

U2 - 10.1002/chem.201704442

DO - 10.1002/chem.201704442

M3 - Article

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SN - 0947-6539

VL - 23

SP - 18282

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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