Visible light-induced metal-free cascade denitrogenative borylation and iodination of nitroarenes
Jun-Wei Li1, Tian-Shun Duan1, Bing Sun1
1School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, P. R. China. fanglinzhang@whut.edu.cn.
Abstract:
An efficient method was developed for the one-pot construction of C-B and C-I via visible light-induced transformation of nitroarenes. This protocol relies on the photochemical properties of nitroarenes under visible light, followed by reduction with B2pin2 and diazotization with BuONO. An array of arylboronates and iodobenzenes were constructed smoothly after excitation with purple LEDs at room temperature. In addition, the synthetic utility of this method was further demonstrated in the late-stage modification of a drug molecule. The advantages of this strategy include metal-free system, mild reaction conditions and acceptable substrate scope.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Aromatic Substitution: Nitration of Benzene
Preparation of Nitriles
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3


