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Issue 15, 2017
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Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature

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Abstract

A new protocol is described for the conversion of heteroarene N-oxides to heteroarylphosphonates through in situ activation with bromotrichloromethane. The N-oxides of isoquinoline, quinoline, quinoxaline and 1,10-phenanthroline were fast transformed into the corresponding heteroarylphosphonates in up to 92% yield under mild conditions in the absence of solvent and metal catalysts. The good functional group tolerance, low cost, feasibility of scale up, and wide availability of reagents make this method a prominent complement to the Hirao coupling.

Graphical abstract: Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature

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Publication details

The article was received on 18 Feb 2017, accepted on 20 Mar 2017 and first published on 20 Mar 2017


Article type: Communication
DOI: 10.1039/C7OB00402H
Citation: Org. Biomol. Chem., 2017,15, 3165-3169
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    Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature

    M. Chen, X. You, L. Bai and Q. Luo, Org. Biomol. Chem., 2017, 15, 3165
    DOI: 10.1039/C7OB00402H

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