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Unsymmetrical CNN-Palladacycles with Geometry-Constrained Iminopyridyl Ligands: an Efficient Precatalyst in Suzuki Coupling for Accessing 1,1-Diarylalkanes from Secondary Benzylic Bromides

Abstract

We have developed a series of unsymmetrical CNN-Palladacycles with geometry-constrained iminopyridyl ligands, which were conveniently prepared through a simple one-pot procedure from the corresponding 2-aryl-5,6,7-trihydroquinolin-8-ones. The Palladium complexes have been fully characterized by 1H and 13C NMR spectroscopy, ESI-mass spectrometry. The X-ray analyses for Pd1 to Pd4 have shown their solid structures. Using these CNN-Palladacycles as the precatalyst, various secondary benzylic bromides have been successfully coupled with arylboronic acids, affording 1,1-diarylalkanes in high selectivity. TON up to 47000 was achieved. Scale-up reaction further demonstrated the practicality and efficiency of the developed strategy.

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Publication details

The article was received on 25 May 2018, accepted on 12 Jul 2018 and first published on 12 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00517F
Citation: Org. Chem. Front., 2018, Accepted Manuscript
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    Unsymmetrical CNN-Palladacycles with Geometry-Constrained Iminopyridyl Ligands: an Efficient Precatalyst in Suzuki Coupling for Accessing 1,1-Diarylalkanes from Secondary Benzylic Bromides

    L. Jin, W. Wei, N. Sun, B. Hu, Z. Shen and X. Hu, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO00517F

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