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An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents†
Arvind K. Yadav,Lal Dhar S. Yadav
RSC Advances Pub Date : 07/30/2014 00:00:00 , DOI:10.1039/C4RA05929H
Abstract

A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N–H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.

Graphical abstract: An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents
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