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Palladium‐Catalyzed Selective Three‐Component Tandem Reaction to Bicyclic 1,2,3‐Triazole Derivatives
Author(s) -
Duan Xinyu,
Huang Xin,
Fu Chunling,
Ma Shengming
Publication year - 2020
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.201901284
Subject(s) - chemistry , bicyclic molecule , cycloaddition , cascade reaction , aryl , allene , alkyne , combinatorial chemistry , catalysis , palladium , sodium azide , azide , intramolecular force , tandem , allylic rearrangement , medicinal chemistry , organic chemistry , alkyl , materials science , composite material
A Pd‐catalyzed highly selective tandem reaction of allenynes, aryl or alkenyl iodides, and sodium azide for the synthesis of bicyclic 1,2,3‐triazole derivatives with a very broad substrate scope including mono‐substituted, 1,3‐disubstituted, and trisubstituted allenynes as well as different types of organic iodides has been reported. Control experiments showed that the reaction went through a cascade allene difunctionalization/Winstein allylic azide rearrangement/intramolecular azide‐alkyne cycloaddition process.