Beilstein J. Org. Chem.2011,7, 781–785, doi:10.3762/bjoc.7.88
moderate yields were achieved [25][26][27][28]. Very recently, our group developed an efficient gold(I)-catalyzed decarboxylative aza-Claisen rearrangement of allylic N-tosylcarbamates for the synthesis of N-tosyl allylic amines [29]. This reaction was performed in water and therefore represented an
Beilstein J. Org. Chem.2010,6, No. 43, doi:10.3762/bjoc.6.43
Lukas J. Goossen Bettina Zimmermann Thomas Knauber Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, Geb. 54, D-67663 Kaiserslautern, Germany 10.3762/bjoc.6.43 Abstract A new protocol for the decarboxylative Heck vinylation of benzoic
and co-workers introduced another version of the Heck reaction in 2002, in which they converted mostly electron-rich aromatic carboxylic acids and alkenes to vinyl arenes with the release of CO2 [21][22][23]. This decarboxylative Heck reaction allows the direct conversion of benzoic acids without
prior activation, but requires the addition of stoichiometric amounts of both base and an oxidant. In the original protocol, an excess of silver carbonate (3 equiv) was added to fulfil these functions. The work of Myers represents a milestone in the development of palladium-catalyzed decarboxylative
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Graphical Abstract
Scheme 1:
Proposed mechanism for the decarboxylative Heck reaction.