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Issue 4, 2017
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A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions

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Abstract

Significant catalyst loading reduction and increased reaction robustness have been achieved for a Pd-catalyzed asymmetric intramolecular C–N coupling through comprehensive mechanistic studies. Detailed kinetic, spectroscopic, and crystallographic analyses revealed that the mono-oxidation of the bis-phosphine ligand is critical for a successful transformation. 31P NMR studies provided an understanding of the inefficient activation of the Pd(OAc)2/(R,R)-QuinoxP* pre-catalyst to form the active bis-phosphine mono-oxide–Pd(0) catalyst with competitive formation of a less active (R,R)-QuinoxP*·PdBr2 complex. Based on these detailed mechanistic studies, a new series of bis-phosphine mono-oxides (BPMO)-ligated Pd(II) pre-catalysts have been rationally developed that allow for reliable and complete catalyst activation which should have general utility in academic and industrial settings.

Graphical abstract: A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions

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Publication details

The article was received on 14 Dec 2016, accepted on 15 Jan 2017 and first published on 19 Jan 2017


Article type: Edge Article
DOI: 10.1039/C6SC05472B
Citation: Chem. Sci., 2017,8, 2841-2851
  • Open access: Creative Commons BY license
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    A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions

    Y. Ji, H. Li, A. M. Hyde, Q. Chen, K. M. Belyk, K. W. Lexa, J. Yin, E. C. Sherer, R. T. Williamson, A. Brunskill, S. Ren, L. Campeau, I. W. Davies and R. T. Ruck, Chem. Sci., 2017, 8, 2841
    DOI: 10.1039/C6SC05472B

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