Li Ya-Xi, Liu Quan-Yun, Zhang Yi, Liu Miao-Miao, Liu Xiaoqian, Shen Mei-Hua, Wang Fang-Ming, Xu Hua-Dong
School of Pharmacy, Changzhou University, Changzhou, 213164, China.
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, 212003, China.
Org Biomol Chem. 2024 Oct 15;22(40):8109-8113. doi: 10.1039/d4ob01056f.
Treatment of alkyl α-(-heteroaryl)-α-diazoacetates with alkylating reagents affords diazoacetate N-heteroarenium salts. These novel 'onium' diazo compounds are mostly yellow solids, displaying increased thermal and acid stability. Their tetrafluoroborates undergo rhodium catalyzed [2 + 1] and Doyle-Kirmse reactions under mild conditions, suggesting the -quaternization an effective means of elimination of -coordination caused catalyst toxicity.
