Synthesis of Azo-Substituted Bicyclo1.1.1pentanes (BCPs) via Base-Promoted Halogen Atom Transfer

Because of the three-dimensional bioisosteric feature, bicyclo1.1.1pentylamines (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.