Abstract
The ability to conduct N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent‐minimised conditions.
Highlights
The ability to conduct N-heterocyclic carbene-catalysed acyl anion chemistry under ball-milling conditions is reported for the first time
Of the many areas of organocatalysis, only secondary amine systems have been well studied under milling conditions, with pioneering contributions from Bolm and co-workers.[6]
It has been established that several reaction manifolds accessible by secondary amine organocatalysis in solution can operate under milling conditions.[7]
Summary
The ability to conduct N-heterocyclic carbene-catalysed acyl anion chemistry under ball-milling conditions is reported for the first time. That a reaction takes place under ball-milling conditions does, not necessarily mean that the process is mechanically driven. We report the first results of combining this NHC activation mode with ball-milling (Figure 1 C).[10]
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