Categories: C-N Bond Formation >
Synthesis of isocyanides
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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.