Blue Light-Induced C─X Insertion and Halogenation Reaction of 3-Diazo-3H-Indoles With Halohydrocarbons
Xuliang Duan1, Jiayan Wang1, Xi Chen1
1School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, China.
Abstract:
Visible light-induced free carbene transfer reactions have attracted much attention over the past decades. Whereas photoinduced C─X insertion and halogenation reactions with halohydrocarbons are rare due to many other competitive carbene transformations. Herein, we disclose a blue light-induced C─X (X = Cl, Br, I) insertion reaction of 3-diazo-3H-indoles with halohydrocarbons, leading to the gem-haloalkylation products in moderate to good yields under mild and neutral conditions. Moreover, starting from the same reagents, the halogenation products could be obtained selectively under acidic conditions in the presence of quantitative AcOH. This method offers a complementary approach for the synthesis of halogenated indoles, which are useful synthetic building blocks and essential structural motifs in bioactive molecules. Further synthetic applications could be envisioned for the construction of C─C and C─X bonds via visible light-induced free carbene transfer reactions.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Reactions at the Benzylic Position: Halogenation
Nucleophilic Aromatic Substitution: Elimination–Addition
Diazonium Group Substitution: –OH and –H
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
