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Issue 34, 2016
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Mechanistic insights into the role of PC- and PCP-type palladium catalysts in asymmetric hydrophosphination of activated alkenes incorporating potential coordinating heteroatoms

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Abstract

The impact of the structural attributes of chiral PC- and PCP-palladium catalysts was investigated in the asymmetric hydrophosphination of various heterocycle-functionalized enone substrates. Due to the architecture of the catalysts, they are confronted with potential catalyst deactivation arising from the coordination of the electron-rich heteroatoms (P, O, N and S) to the metal center. A systematic variation of the location and identity of the heteroatoms demonstrated the impact of structural modifications on the substrates, which have a significant influence on both yields (16–99%) and enantioselectivities (0–99%). A detailed discussion on the distinct catalytic mechanisms (intra- vs. inter-molecular addition) provides important information to explain the results obtained.

Graphical abstract: Mechanistic insights into the role of PC- and PCP-type palladium catalysts in asymmetric hydrophosphination of activated alkenes incorporating potential coordinating heteroatoms

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Publication details

The article was received on 29 Jun 2016, accepted on 21 Jul 2016 and first published on 22 Jul 2016


Article type: Paper
DOI: 10.1039/C6DT02588A
Citation: Dalton Trans., 2016,45, 13449-13455
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    Mechanistic insights into the role of PC- and PCP-type palladium catalysts in asymmetric hydrophosphination of activated alkenes incorporating potential coordinating heteroatoms

    X. Yang, Y. Jia, W. S. Tay, Y. Li, S. A. Pullarkat and P. Leung, Dalton Trans., 2016, 45, 13449
    DOI: 10.1039/C6DT02588A

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