N‐Heterocyclic Carbene Copper(I) Rotaxanes Mediate Sequential Click Ligations with All Reagents Premixed

Autor:	Chi-You Tsai, Chien-Chen Lai, Sheng-Hsien Chiu, Shie-Ming Peng, Yi-Hung Liu, Fang-Che Hsueh
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Steric effects Rotaxane 010405 organic chemistry Chemistry Alkyne General Chemistry General Medicine 010402 general chemistry 01 natural sciences Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound Polymer chemistry Click chemistry Azide Carbene
Zdroj:	Angewandte Chemie. 132:11374-11378
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202001398
Popis:	We have prepared NHC-CuI complexes with a rotaxane structure and used them as sterically sensitive catalysts for one-pot sequential copper-catalyzed azide/alkyne cycloadditions in solutions containing all of the coupling partners premixed in unprotected form. Most notably, a photolabile and sterically encumbered complex first catalyzed the coupling of a less bulky azide/alkyne pair; after removing the protective macrocyclic component from the rotaxane structure, through irradiation with light, the exposed dumbbell-shaped NHC-CuI complex catalyzed the second click reaction of a bulkier azide/alkyne pair. Using this approach, we obtained predominantly, from a single sealed pot, a bis-triazole product (84 %) from a mixture of two sterically distinct azides and a diyne.
Databáze:	OpenAIRE
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