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- Title
N‐Heterocyclic Carbene Copper(I) Rotaxanes Mediate Sequential Click Ligations with All Reagents Premixed.
- Authors
Hsueh, Fang‐Che; Tsai, Chi‐You; Lai, Chien‐Chen; Liu, Yi‐Hung; Peng, Shie‐Ming; Chiu, Sheng‐Hsien
- Abstract
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.
- Subjects
ROTAXANES; AZIDATION; COPPER; RING formation (Chemistry); AZIDES; CATALYSTS
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 28, p11374
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202001398