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Zeo‐Click Synthesis: Copper‐Zeolite‐Catalyzed Synthesis of Ynamides
Author(s) -
Harkat Hassina,
Borghèse Sophie,
Nigris Matteo De,
Kiselev Serguei,
Bénéteau Valérie,
Pale Patrick
Publication year - 2014
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.201400189
Subject(s) - chemistry , zeolite , catalysis , copper , alkyl , combinatorial chemistry , heterogeneous catalysis , nitrogen , reaction conditions , organic chemistry , coupling reaction , polymer chemistry
Copper(I)‐zeolites, especially copper(I)‐ultra stable Y zeolite (USY), are very efficient heterogeneous catalysts for the coupling of functionalized 1‐bromoalkynes and various nitrogen derivatives. Under these conditions, sulfonylated alkyl‐ or arylamines and various N‐heterocycles, such as oxazolidinones or indoles, could be efficiently transformed into the corresponding N ‐alkynyl derivatives. However, imidazoles gave addition products rather than coupling products. The reaction conditions proved compatible with a variety of functional and protecting groups. Such zeolitic catalysts can be recycled and reused at least five times without significant deactivation. Low catalyst loading could be used (4 mol%) and as low as 0.8 mol% of this heterogeneous copper catalyst still gave good conversion and yields.