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Issue 7, 2014
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Phosphine-free Heck reaction: mechanistic insights and catalysis “on water” using a charge-tagged palladium complex

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Abstract

A novel Pd-complex with a charge tag (imidazolium cation) was applied for online monitoring of the neutral Heck reaction by electrospray ionization (tandem) mass spectrometry – ESI-MS(/MS). The results shed light on the mechanism of the reaction, whereas the charge-tagged ligand also allowed the unprecedented MS monitoring of Pd2+ reduction to Pd0. Key reaction intermediates associated with Pd catalysis could also be detected and characterized due to the presence of the charge tag on the Pd-complex. DFT calculations supported the proposed mechanism. The new charge-tagged Pd-complex is also shown to function as an active catalyst “on water” with the advantage of using cheaper and less reactive aryl chloride substrates in a phosphine-free version of the Heck reaction.

Graphical abstract: Phosphine-free Heck reaction: mechanistic insights and catalysis “on water” using a charge-tagged palladium complex

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Supplementary files

Article information


Submitted
26 Feb 2014
Accepted
10 Apr 2014
First published
11 Apr 2014

New J. Chem., 2014,38, 2958-2963
Article type
Paper

Phosphine-free Heck reaction: mechanistic insights and catalysis “on water” using a charge-tagged palladium complex

M. R. dos Santos, R. Coriolano, M. N. Godoi, A. L. Monteiro, H. C. B. de Oliveira, M. N. Eberlin and B. A. D. Neto, New J. Chem., 2014, 38, 2958 DOI: 10.1039/C4NJ00285G

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