Introduction
Cyanation of carbonyl compounds is one of the most powerful procedures for the synthesis of polyfunctionalized molecules. Compared to various cyanating reagents such as KCN, NaCN, and HCN, trimethylsilyl cyanide (TMSCN) is a safer and more effective cyanide source for nucleophilic addition to carbonyl compounds under mild conditions.
[1]
[2]
Asymmetric addition of TMSCN to carbonyl compounds and subsequent hydrolysis produces chiral cyanohydrins.
[3]
The reaction of an epoxide with TMSCN leads to formation of either trimethylsilyloxy nitrile (C-nucleophilic attack) or trimethylsiloxy isocyanide (N-nucleophilic attack) depending on the nature of the catalyst, due to the ambident nucleophilic character of TMSCN.
[4]
Cyanation of nucleophilic alkynes as an easy approach to substituted α-cyanoenamines is another ability of TMSCN.
[5]
Recently, TMSCN was used as a functional, yet non-classical isonitrile, for the synthesis of 3-aminoimidazo[1,2-a]pyridines.
[6]