Synthesis of catenane structures via ring-closing metathesis

Marcus Weck, Bernhard Mohr, Jean Pierre Sauvage, Robert H. Grubbs

Research output: Contribution to journalArticle

Abstract

This study presents a detailed description of a synthetic strategy to obtain catenane architectures through ring-closing metathesis. The approach is based on phenanthroline-based ligands containing terminal olefinic units that were designed to coordinate in a tetrahedral arrangement around a copper atom. Treatment of the assembled copper complexes with ruthenium catalyst 1 resulted in [2]catenates in high yields of 88-92%. Demetalation produced the corresponding [2]catenand in nearly quantitative yields. Hydrogenation of the catenates with Crabtree's catalyst and subsequent demetalation yielded fully saturated catenands. The presently described procedure makes [2]catenanes very accessible since the synthetic route consists of six steps (Schemes 2 and 4) from commercially available 1,10-phenanthroline, the overall yield being 51%.

Original languageEnglish (US)
Pages (from-to)5463-5471
Number of pages9
JournalJournal of Organic Chemistry
Volume64
Issue number15
DOIs
StatePublished - Jul 23 1999

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Catenanes
Copper
Catalysts
Phenanthrolines
Ruthenium
Hydrogenation
Ligands
Atoms
catenane
1,10-phenanthroline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of catenane structures via ring-closing metathesis. / Weck, Marcus; Mohr, Bernhard; Sauvage, Jean Pierre; Grubbs, Robert H.

In: Journal of Organic Chemistry, Vol. 64, No. 15, 23.07.1999, p. 5463-5471.

Research output: Contribution to journalArticle

Weck, Marcus ; Mohr, Bernhard ; Sauvage, Jean Pierre ; Grubbs, Robert H. / Synthesis of catenane structures via ring-closing metathesis. In: Journal of Organic Chemistry. 1999 ; Vol. 64, No. 15. pp. 5463-5471.
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