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- Title
Macrocyclization by Rhodium-Catalyzed Cross-Cyclotrimerization of L-Shaped Diynes with Di- tert-butyl Acetylenedicarboxylate: Effect of Bent Linkers of Diynes.
- Authors
Nishigaki, Shuhei; Miyauchi, Yuta; Noguchi, Keiichi; Ito, Hideto; Itami, Kenichiro; Shibata, Yu; Tanaka, Ken
- Abstract
The effects of bent linkers in diynes on the efficiency and selectivity of intermolecular macrocyclization by the rhodium-catalyzed sequential cross-cyclotrimerization of L-shaped diynes and di- tert-butyl acetylenedicarboxylate was investigated. A bulky triethylsilyl-protected cyclohexa-1,4-dienediol-linked diyne reacted with di- tert-butyl acetylenedicarboxylate to give the corresponding 16-membered macrocycle as well as the 12-membered macrocycle. Aromatization of the thus-obtained 12-membered macrocycle through desilylation followed by reductive aromatization with SnCl2 and HCl afforded a [12]cycloparaphenylenehexacarboxylate. The use of a conformationally flexible methoxymethyl-protected cyclohexanediol-linked diyne increased the yield of the corresponding 16-membered macrocycle, although oxidative aromatization leading to the corresponding cycloparaphenylenes was unsuccessful.
- Subjects
RHODIUM catalysts; MACROCYCLIC compounds; AROMATIZATION; AROMATIC compound synthesis; PLATINUM group catalysts
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 27, p4668
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600909