Premium
Improved Synthesis of 1,2,3‐Triazolium Salts via Oxidative [3+2] Cycloaddition of Triazenes with Alkynes and Their Deprotonative Functionalization
Author(s) -
Sawaguchi Daiki,
Hayakawa Shunsuke,
Sakuma Masaaki,
Niitsuma Kenta,
Kase Daiya,
Michii Shota,
Ozawa Miyuki,
Sakai Yusuke,
Sakamaki Kentaro,
Ueyama Kyohei,
Haraguchi Ryosuke
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100033
Subject(s) - chemistry , surface modification , mesoionic , cycloaddition , combinatorial chemistry , substrate (aquarium) , oxidative phosphorylation , scope (computer science) , organic chemistry , catalysis , biochemistry , oceanography , computer science , programming language , geology
Abstract 1,2,3‐Triazolium units are present in various functionalized molecules, including mesoionic carbenes, organocatalysts, and anion recognition receptors. While the oxidative [3+2] cycloaddition of triazenes with alkynes is one of the most efficient methods to construct the 1,2,3‐triazolium skeleton, the effect of reaction parameters and substrate scope in the reaction has not been fully studied. Herein, we developed a practical protocol for the synthesis of 1,2,3‐triazolium salts and significantly expanded the substrate scope of triazenes and alkynes. Also, an efficient method for the deprotonative functionalization of 1,2,3‐triazolium salts was achieved.