Issue 16, 2018

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 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

Supplementary files

Article information

Article type
Research Article
Submitted
25 máj 2018
Accepted
12 júl 2018
First published
12 júl 2018

Org. Chem. Front., 2018,5, 2484-2491

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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