A novel three-component coupling reaction of arynes, isocyanides, and cyanoformates: A straightforward access to cyano-substituted iminoisobenzofurans
Iminoisobenzofuran derivatives have been prepared in moderate yields by the palladium-catalyzed three-component coupling reaction of arynes, isocyanides, and cyanoformates.
New entry to the synthesis of α-iminonitriles by Lewis acid mediated isomerization of cyano-substituted iminoisobenzofurans prepared by palladium-catalyzed three-component coupling of arynes, isocyanides, and cyanoformates
A variety of α-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)2(dppf)] (BF4)2 as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. α-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into α-iminonitriles was observed.