Base-Induced Highly Regioselective Synthesis of <i>N</i><sup>2</sup>-Substituted 1,2,3-Triazoles under Mild Conditions in Air
Jian Ji, Cong Guan, Qinghua Wei, Xuwen Chen, Yun Zhao, Shunying Liu
Abstract
We developed a highly regioselective base-induced synthesis of N2-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an SN2-like mechanistic pathway to explain the high N2-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72–90%).
Topics & Concepts
RegioselectivityChemistryAlkylSN2 reactionBase (topology)Substrate (aquarium)Combinatorial chemistrySulfonylMedicinal chemistryOrganic chemistryStereochemistryCatalysisOceanographyMathematical analysisMathematicsGeologyClick Chemistry and ApplicationsCyclopropane Reaction MechanismsSynthesis and Biological Evaluation