The synthesis of arylcyanamides: a copper-catalyzed consecutive desulfurization and C–N cross-coupling strategy

Abstract

A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thioureaviadesulphurization/C–N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described.

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

“…Based on these experimental investigations and the available literature [37,[40][41][42][43][44][45][46][47][48][49][50], the mechanism for the formation of the final product 2-phenylaminobenzimidazole is very much similar to the mechanism reported for cobalt catalysis [37] (see supporting information Scheme S1).…”

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

“…Since the resulting product N-phenylcyanamide 2a is widely applied as an estimable building block in the direct and efficient synthesis of many bioactive molecules, this protocol is particularly useful. Examples include tetrazolamine 3, 22 urea 4, 23 amide 5, 24 guanidine 6, 25 2-aminoquinazolin-4-one 7, 26 and aminobenzonitrile 8. 27 These representative transformations clearly demonstrate the versatility of cyanamides in organic chemistry.…”

Organo-cyanamides: convenient reagents for catalytic amidation of carboxylic acids

“…Although a comparable yield was obtained, the preparation of 11 is more difficult than NCTS due to the requirement of two-step operation or highly toxic bromoacetonitrile. 14 Therefore, the easily available NCTS was selected as a model substrate to conduct this reaction. It should be noted that N -cyano-4-methylbenzenesulfonamide 12 and aniline 13 failed to give 3aa under the standard conditions (Scheme 4c and d).…”