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Molecules 2013, 18(3), 2788-2802; doi:10.3390/molecules18032788

Synthesis of New BINAP-Based Aminophosphines and Their 31P-NMR Spectroscopy

Department Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW, 2109, Australia
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Received: 16 January 2013 / Revised: 8 February 2013 / Accepted: 21 February 2013 / Published: 1 March 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

BINAP aminophosphines are prevalent N,P-bidentate, chiral ligands for asymmetric catalysis. While modification via the BINAP-nitrogen linkage is well explored and has provided a diverse body of derivatives, modification of the other substituents of the phosphorous center is another avenue in generating new congeners of this important class of chiral ligands. Herein reported are new BINAP aryl aminophosphines with electron rich or deficient substituents on the aryl rings. This scalable synthesis converted readily available starting material, (S)-BINOL, to a key intermediate (S)-NOBIN, from which the final chiral aminophosphines were prepared via a palladium-catalyzed, phosphonylation reaction. The aryl substituents are able to modify the electronic properties of the phosphorous center as indicated by the range of 31P-NMR shifts of these new ligands. A computational analysis was performed to linearly quantitate contributions to the 31P-NMR shifts from both resonance and field effects of the substituents. This correlation may be useful for designing and preparing other related aminophosphines with varying ligand properties.
Keywords: bidentate ligands; BINAP aryl aminophosphines; substituent effects; NOBIN; MAP bidentate ligands; BINAP aryl aminophosphines; substituent effects; NOBIN; MAP
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Anstiss, C.; Karuso, P.; Richardson, M.; Liu, F. Synthesis of New BINAP-Based Aminophosphines and Their 31P-NMR Spectroscopy. Molecules 2013, 18, 2788-2802.

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