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October 14, 2006The Journal of Organic Chemistry90 citations

ESI-MS Detection of Proposed Reaction Intermediates in the Air-Promoted and Ligand-Modulated Oxidative Heck Reaction

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PEPer‐Anders EnquistPNPeter NilssonPSPer J. R. Sjöberg

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Abstract

Electrospray ionization mass spectrometry (ESI-MS) and subsequent MS/MS analyses were used to directly detect palladium-containing cationic reaction intermediates in a ligand controlled palladium(II)-catalyzed oxidative Heck arylation. All potential intermediates were observed as dmphen-ligated palladium(II) species, suggesting that the dmphen bidentate ligand is attached to the metal center during the entire catalytic cycle. The study supports previous mechanistic propositions and provides new information regarding the composition of aryl-containing Pd(II) complexes in an ongoing oxidative Heck reaction. In addition, sodium acetate was found to be a useful base alternative to previously used tertiary amines.

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Enquist et al. (2006) studied this question.

synapsesocial.com/papers/6a94ca24b1b9682fb47c3b31https://doi.org/10.1021/jo061437d
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