Atroposelective Three-Component Coupling of Cyclic Diaryliodoniums and Sodium Cyanate Enabled by the Dual-Role of Phenol
Shan Yang
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
Search for more papers by this authorTianze Zheng
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
Search for more papers by this authorDr. Longhui Duan
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
Search for more papers by this authorDr. Xiaoping Xue
College of Science, Henan Agricultural University, Zhengzhou, Henan, 450002 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Zhenhua Gu
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
College of Materials and Chemical Engineering, Minjiang University, Fuzhou, Fujian, 350108 P. R. China
Search for more papers by this authorShan Yang
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
Search for more papers by this authorTianze Zheng
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
Search for more papers by this authorDr. Longhui Duan
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
Search for more papers by this authorDr. Xiaoping Xue
College of Science, Henan Agricultural University, Zhengzhou, Henan, 450002 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Zhenhua Gu
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 P. R. China
College of Materials and Chemical Engineering, Minjiang University, Fuzhou, Fujian, 350108 P. R. China
Search for more papers by this authorAbstract
A copper-catalyzed atroposelective ring-opening reaction of cyclic diaryliodoniums, sodium cyanate (NaOCN) and phenols is reported. The reaction chemoselectively affords axially chiral carbamates by sequential coupling of cyclic diaryliodonium and NaOCN, followed by phenol. Mechanistic investigations revealed that phenol is not only a reagent to trap highly active intermediate isocyanates, but it also activates the copper catalyst as a standby ligand. The carbamates were readily transformed into highly functionalized urea derivatives within a simple nucleophilic substitution reaction.
Conflict of interest
The authors declare no conflict of interest.
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