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General Cycloaddition Between a Trimethylsilyl‐Capped Alkyne and an Azide Catalyzed by an N‐Heterocyclic Carbene‐Copper Complex and Pyridine‐Biscarboxamide
Author(s) -
Xu Haochen,
Sun Zhihua
Publication year - 2016
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.201501171
Subject(s) - chemistry , alkyne , cycloaddition , carbene , azide , trimethylsilyl , aryl , combinatorial chemistry , pyridine , catalysis , polymer chemistry , photochemistry , organic chemistry , alkyl
With an externally provided catalytic amide facilitator and an N‐heterocyclic carbene‐copper (NHC‐Cu) complex, the cycloaddition of an azide and a trimethylsilyl (TMS)‐capped alkyne can proceed smoothly. This protocol can be applied to a variety of TMS‐capped substrates, with electron‐rich alkynes generally giving higher yields and nitroaromatic alkynes giving lower yields. For special applications of this protocol, a substrate containing both a terminal alkyne and a TMS‐capped alkyne can sequentially react with different azides without isolation of intermediates; and a macrocyclic product can also be formed efficiently without the complication of polymer formation.