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Auto‐Tandem Catalysis: Pd II ‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
Author(s) -
Lamb Claire J. C.,
Nderitu Bryan G.,
McMurdo Gemma,
Tobin John M.,
Vilela Filipe,
Lee AiLan
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704442
Subject(s) - dehydrogenation , cyclopentane , chemistry , catalysis , tandem , heck reaction , oxidative phosphorylation , oxidative addition , organic chemistry , medicinal chemistry , palladium , biochemistry , materials science , composite material
Abstract 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.