Tong-Hao Zhu, Xiao-Ping Xu, Jia-Jia Cao, Tian-Qi Wei, Shun-Yi Wang* (汪顺义) and Shun-Jun Ji*(纪顺俊)
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
Adv. Synth. Catal. 2014, 356, 509–518.
Cobalt(II) acetylacetonate-catalyzed isocyanide insertion reactions with amines utilizing tert-butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles under the general reaction conditions in up to 96% yields, respectively. The intermediate amino methylidyneaminiums, initiated by cobalt(II) acetylacetonate-catalyzed reactions of isocyanides with amines, could be easily trapped by different nucleophiles such as water, sulfur, and intramolecular nucleophilic functional groups. This method provides a simple, general and practical protocol for the divergent synthesis of ureas, thioureas and azaheterocycles.
链接:
//onlinelibrary.wiley.com/doi/10.1002/adsc.201300745/abstract