Categories: C-N Bond Formation >
Synthesis of isocyanides
Treatment of benzyl halides with silver salts and trimethylsilyl cyanide followed by cleavage of the carbon-silicon bond directly afforded the corresponding isocyanides.
Y. Kitano, T. Manoda, T. Miura, K. Chiba, M. Tada, Synthesis, 2006, 405-410.
A one-pot reaction of alcohols with trimethylsilyl cyanide and methanesulfonic acid with subsequent neutralization by triethylamine and dehydration by tosyl chloride and pyridine gave the corresponding isocyanides in good yields. This method enables the synthesis of tertiary and benzylic isocyanides.
I. Okada, Y. Kitano, Synthesis, 2011, 3997-4002.