# Aluminum-Centered C–C Heterocoupling of Organonitriles

## TL;DR

This paper describes a new method for forming C–C bonds between different nitriles using an aluminum-based compound.

## Contribution

The study introduces a selective aluminum-mediated C–C heterocoupling of organonitriles.

## Key findings

- The compound reacts with both aryl- and alkyl-substituted nitriles.
- The reaction enables the selective formation of diazabutadienylaluminate dianions with two distinct N=C substituents.

## Abstract

The C-tert-butyl substituted azacyclopropenylaluminate,
[(SiNDipp)­Al-η2-{NCt-Bu}­K]∞ (SiNDipp = (CH2SiMe2NDipp)2) reacts with both aryl- and alkyl-substituted
nitriles. In contrast to previously reported attempts to effect C–C
bond formation between two dissimilar nitriles, these reactions enable
the completely discriminating heterocoupling of t-BuCN to provide diazabutadienylaluminate dianions that bear two
differentiated NC substituents.