Reductive generation of stable, five-membered N,N′-diamidocarbenes?

Chemical Communications Pub Date: 2014-03-27 DOI: 10.1039/C4CC00846D

Abstract

The synthesis of the first stable, five-membered N,N′-diamidocarbenes (DACs), including a differentially N-substituted derivative, was achieved via the reduction of a geminal dichloride precursor using potassium. Key differences between the reactivity of the five-membered DACs and their six-membered congeners were observed, including an ability to insert into electron-rich C–H bonds.

Graphical abstract: Reductive generation of stable, five-membered N,N′-diamidocarbenes
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