Cross-dehydrogenative N–N couplings

Chemical Science, vol. 12, pp. 14343–14352

Abstract

The relatively high electronegativity of nitrogen makes N-N bond forming cross-coupling reactions particularly difficult, especially in an intermolecular fashion. The challenge increases even further when considering the case of dehydrogenative N-N coupling reactions, which are advantageous in terms of step and atom economy, but introduce the problem of the oxidant in order to become thermodynamically feasible. Indeed, the oxidizing system must be designed to activate the target N-H bonds, while at the same time avoid undesired N-N homocoupling as well as C-N and C-C coupled side products. Thus, preciously few intermolecular hetero N-N cross-dehydrogenative couplings exist, in spite of the central importance of N-N bonds in organic chemistry. This review aims at analyzing these few rare cases and provides a perspective for future developments.

Authors 3

1. Alexis Tabey Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

2. Pooja Y. Vemuri Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

3. Frédéric W. Patureau corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany