Cu(II) catalyzed imine C–H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles

Guin, Srimanta ; Ghosh, Tuhin ; Rout, Saroj Kumar ; Banerjee, Arghya ; Patel, Bhisma K. (2011) Cu(II) catalyzed imine C–H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles Organic Letters, 13 (22). pp. 5976-5979. ISSN 1523-7060

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Official URL: https://pubs.acs.org/doi/abs/10.1021/ol202409r

Related URL: http://dx.doi.org/10.1021/ol202409r

Abstract

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C–H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C–H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.

Item Type:Article
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ID Code:113918
Deposited On:30 Apr 2018 12:20
Last Modified:30 Apr 2018 12:20

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