Synthesis of Azo-Substituted Bicyclo[1.1.1]pentanes (BCPs) via Base-Promoted Halogen Atom Transfer
Yanchuang Zhao, Jing Zhang, Zhi-Jin Zhan, Qiujin Fan, Xu‐Qiong Xiao, Ying Bai, Shao‐Fei Ni, Xinxin Shao
Abstract
Because of the three-dimensional bioisosteric feature, bicyclo[1.1.1]pentylamines (BCPAs) are valuable scaffolds in synthetic chemistry and medicinal chemistry. Here, we report a Halogen Atom Transfer (XAT) mediated radical C-N coupling between C3-iodo-BCPs and diazonium salts in the presence of base. Similarly, a multicomponent reaction (MCR) enables the simultaneous construction of the C-C bond and C-N bond simultaneously. Versatile roles of diazonium salts were also explored.
Topics & Concepts
ChemistryHalogenHalogen bondCombinatorial chemistryBase (topology)Bicyclic moleculeAtom-transfer radical-polymerizationAtom (system on chip)Organic chemistryPolymerMathematical analysisCopolymerAlkylMathematicsComputer scienceEmbedded systemRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods