Visible-Light-Promoted Site-Selective N1-Alkylation of Benzotriazoles with α-Diazoacetates
Jingya Yang1, Jiaokui Duan1, Ganggang Wang1
1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.
Abstract:
A visible-light-promoted highly site-selective N1-alkylation of benzotriazoles with diazo compounds has been achieved under mild and metal-free conditions. Using cheap, readily available p-benzoquinone (PBQ) as a catalyst, a wide range of benzotriazoles and diazo compounds are reacted, providing N1-alkylated benzotriazoles in moderate to excellent yields with excellent N1-selectivities. Preliminary mechanistic studies suggest that a radical process accounts for the exclusive site-selectivity of this transformation.
More Related Videos
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Nitration of Benzene
Diazonium Group Substitution: –OH and –H
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
