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Visible Light‐Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis
Author(s) -
Yang Liangfeng,
Li Haifeng,
Du Yijun,
Cheng Kai,
Qi Chenze
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900603
Subject(s) - chemistry , photoredox catalysis , aryl , catalysis , photochemistry , visible spectrum , photocatalysis , quenching (fluorescence) , combinatorial chemistry , transition metal , decarboxylation , organic chemistry , alkyl , fluorescence , physics , optoelectronics , quantum mechanics
A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely‐functionalized aryl alkynes could be synthesized under mild, neutral and transition metal‐free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal‐free operation, another key point of this method is that the organic dye catalyst acts as an excited‐state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination.