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Issue 7, 2015
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Highly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides

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Abstract

Platinum complexes modified with a chiral non-racemizing SPO preligand 1 have been applied in the hydration of aromatic nitriles. [Pt(1)3Cl]Cl formed readily from Pt(COD)Cl2. The chiral secondary phosphine oxide complex showed moderate activity in the hydration of para- and meta-substituted benzonitriles, but failed in converting the ortho-substituted derivatives. The hydride complex PtH(PR2OH)(PR2O–H⋯OR2P) (PR2OH = 1) formed from Pt(PPh3)4 and 1, and the cationic complex derived from [Pt(1)3Cl]Cl via direct chloride abstraction with AgNO3 were proven to be considerably more active, allowing us to extend the scope to the hydration of ortho-substituted aromatic nitriles, including axially chiral [1,1′-binaphthalene]-2,2′-dicarbonitrile. In the hydration of the racemic dinitrile, successful kinetic resolution has been achieved. The catalysts derived from non-racemizing 1 are the first chiral transition metal–SPO complexes that provide kinetic resolution in the hydration of a racemic chiral nitrile.

Graphical abstract: Highly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides

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Publication details

The article was received on 29 Apr 2015, accepted on 26 May 2015 and first published on 26 May 2015


Article type: Paper
DOI: 10.1039/C5CY00627A
Catal. Sci. Technol., 2015,5, 3822-3828

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    Highly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides

    H. Gulyás, I. Rivilla, S. Curreli, Z. Freixa and P. W. N. M. van Leeuwen, Catal. Sci. Technol., 2015, 5, 3822
    DOI: 10.1039/C5CY00627A

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