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Issue 16, 2018
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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

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Abstract

We 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 were fully characterized by 1H and 13C NMR spectroscopy and ESI-mass spectrometry. X-ray analyses of 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 with high selectivity. A TON of up to 47 000 was achieved. The scale-up reaction further demonstrated the practicality and efficiency of the developed strategy.

Graphical abstract: Unsymmetrical CNN-palladacycles with geometry-constrained iminopyridyl ligands: an efficient precatalyst in Suzuki coupling for accessing 1,1-diarylalkanes from secondary benzylic bromides

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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., 2018,5, 2484-2491
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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, 5, 2484
    DOI: 10.1039/C8QO00517F

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