Synlett ( IF 1.7 ) Pub Date : 2014-04-11 , DOI: 10.1055/s-0033-1341246 Shanyan Mo
N-Cyano-N-phenyl-p-toluenesulfonamide (NCTS) is a bench-stable colorless solid (mp 85–87 °C)[1]. It is commercially available and can be readily synthesized by Kurzer’s method[2] on a large scale from inexpensive phenylurea and p-toluenesulfonyl chloride with pyridine as solvent[2] (Scheme [1]). The preparation of NCTS does not require the use of toxic cyanogen halides; thus, comparing to other cyanating reagent, such as p-toluenesulfonyl cyanide,[3] N-cyanobenzimidazole,[4] N-cyanophthalimide[4b] [c] and especially metal cyanide[5], NCTS can be accessed more safely.
Owing to the N–CN bond, NCTS serves as an electrophilic cyanating reagent. In addition, NCTS is employed in the direct C–H cyanation to a variety of (hetero)arenes. The byproduct for the cyanation using NCTS is N-phenyl-p-toluenesulfonamide, an environmentally benign compound. The cyanation process features the advantages of wide substrate scopes, safe operations, and moderate to excellent yields.
中文翻译:
N-氰基-N-苯基-对甲苯磺酰胺
N-氰基-N-苯基-对甲苯磺酰胺(NCTS)是一种稳定的无色固体(熔点85-87°C)[1]。它是可商购的,可以很容易地用Kurzer的方法[2]以廉价的苯基脲和对甲苯磺酰氯为吡啶,以吡啶为溶剂[2]进行大规模合成(方案[1])。NCTS的制备不需要使用有毒的卤化氰。因此,与其他氰化试剂(例如对甲苯磺酰氰,[3] N-氰基苯并咪唑,[4] N-氰基邻苯二甲酰亚胺[4b] [c],尤其是金属氰化物[5])相比,可以更安全地使用NCTS。
由于N -CN键,NCTS可以用作亲电子氰化试剂。另外,NCTS用于直接C–H氰化成各种(杂)芳烃。使用NCTS进行氰化的副产物是N-苯基-对甲苯磺酰胺,一种对环境无害的化合物。氰化工艺的优点是底物范围广,操作安全且产率中等至优异。