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Zeo‐Click Chemistry: Copper(I)–Zeolite‐Catalyzed Cascade Reaction; One‐Pot Epoxide Ring‐Opening and Cycloaddition
Author(s) -
Boningari Thirupathi,
Olmos Andrea,
Reddy Benjaram M.,
Sommer Jean,
Pale Patrick
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000802
Subject(s) - chemistry , cycloaddition , epoxide , catalysis , copper , sodium azide , click chemistry , zeolite , ring (chemistry) , azide , organic chemistry , stereoselectivity , combinatorial chemistry , polymer chemistry
Abstract Copper(I)‐modified zeolites, especially Cu I –USY, proved to be very efficient catalysts in multi‐component reactions of epoxides with sodium azide and terminal alkynes. Such catalysts allow highly regio‐ and stereoselective syntheses ofhydroxymethylated triazoles. These heterogeneous, modified zeolites can easily be recovered and reused. Moreover, the cascade reaction was best performed in water at room temperature, rendering all the processes truly green. Detailed investigations revealed the role the Cu I ‐modified zeolites play both during the epoxide ring‐opening and cycloaddition steps.