Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage.
A gold-catalyzed nitrogenation of alkynes for the synthesis of carbamides and amino tetrazoles through C-C and C≡C bond cleavages is described. A diverse set of functionalized carbamide and amino tetrazole derivatives were selectively constructed under mild conditions. The chemoselectivity can be easily switched by the selection of the acid additives. The reaction is characterized by its broad substrate scope, direct construction of high value products, easy operation under air, and mild conditions at room temperature. This chemistry provides a way to transform alkynes by splitting the substrate into three parts.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China).
Chong
C
Qin
Department of Chemistry, University of South Florida, Tampa, FL 33620 (USA).
Yijin
Y
Su
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China).
Tao
T
Shen
Department of Chemistry, University of South Florida, Tampa, FL 33620 (USA). xmshi@usf.edu.
Xiaodong
X
Shi
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China). jiaoning@pku.edu.cn.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China). jiaoning@pku.edu.cn.
Ning
N
Jiao
CC bond cleavage; carbamides; gold; rearrangements; tetrazoles