text: NHCs are often strongly basic (the pKa value of the conjugate acid of an imidazol-2-ylidene was measured at ca. 24) and react with oxygen. Clearly these reactions are performed using air-free techniques, avoiding compounds of even moderate acidity. Although imidazolium salts are stable to nucleophilic addition, other non-aromatic salts are not (i.e. formamidinium salts).
  In these cases, strong unhindered nucleophiles are avoided whether they are generated in situ or are present as an impurity in other reagents (such as LiOH in BuLi).
  Several approaches have been developed in order to prepare stable carbenes, these are outlined below.