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Issue 9, 2014
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t-BuXPhos: a highly efficient ligand for Buchwald–Hartwig coupling in water

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Abstract

An efficient and versatile ‘green’ catalytic system for the Buchwald–Hartwig cross-coupling reaction in water is reported. In an aqueous micellar medium, the combination of t-BuXPhos with [(cinnamyl)PdCl]2 showed excellent performance for coupling arylbromides or chlorides with a large set of amines, amides, ureas and carbamates. The method is functional-group tolerant, proceeds smoothly (30 to 50 °C) and provides rapid access to the target compounds in good to excellent isolated yields. When applied to the synthesis of a known NaV1.8 modulator, this method led to a significant improvement of the E-factor in comparison with classical organic synthesis.

Graphical abstract: t-BuXPhos: a highly efficient ligand for Buchwald–Hartwig coupling in water

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Publication details

The article was received on 09 May 2014, accepted on 01 Jul 2014 and first published on 01 Jul 2014


Article type: Paper
DOI: 10.1039/C4GC00853G
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Citation: Green Chem., 2014,16, 4170-4178
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    t-BuXPhos: a highly efficient ligand for Buchwald–Hartwig coupling in water

    P. Wagner, M. Bollenbach, C. Doebelin, F. Bihel, J. Bourguignon, C. Salomé and M. Schmitt, Green Chem., 2014, 16, 4170
    DOI: 10.1039/C4GC00853G

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