Straightforward Path to Cyanoformamides

Straightforward Path to Cyanoformamides

Author: ChemistryViews

Cyanoformamides (RHN–C(=O)–CN) are useful intermediates in organic synthesis, e.g., for the preparation of heterocycles. However, their synthesis can require toxic CN-containing species and other hazardous reactants.

Vittorio Pace, University of Vienna, Austria, and University of Turin, Italy, and colleagues have developed a method for the straightforward preparation of cyanoformamides that is based on cyanide release from a suitable precursor in the presence of electrophilic isocyanates. The team used PhMe2SiCN as a cyanide “reservoir”, which releases CN at a fast rate upon the formation and collapse of a complex with the Lewis base potassium tert-amylate (KOtAm).

The researchers reacted a variety of widely available isocyanates with different aromatic or aliphatic substituents with PhMe2SiCN in the presence of catalytic amounts of KOtAm in tetrahydronfuran (THF). The desired cyanoformamides were obtained within 1 min in high to excellent yields.


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