Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 3, Pages 395-404Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600264
Keywords
metathesis; N-heterocyclic carbenes; ruthenium; Schiff bases; water; X-ray diffraction
Categories
Funding
- NCRR NIH HHS [P41 RR002301] Funding Source: Medline
- NIGMS NIH HHS [R01 GM044783-17, R01 GM044783] Funding Source: Medline
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Tuning the electronic and steric environment of olefin metathesis catalysts with specialized ligands can adapt them to broader applications, including metathesis in aqueous solvents. Bidentate salicylaldimine ligands are known to stabilize ruthenium alkylidene complexes, as well as allow ring-closing metathesis in protic media. Here, we report the synthesis and characterization of exceptionally robust olefin metathesis catalysts bearing both bidenlate salicylaldimine and N-heterocyclic carbene ligands, including a trimethylammonium-functionalized complex adapted for polar solvents. NMR spectroscopy and X-ray crystallographic analysis confirm the structures of the complexes. Although the N-heterocyclic carbene-salicylaldimine ligand combination limits the activity of these catalysts in non-polar solvents, this pairing enables efficient ring-closing metathesis of both dienes and enynes in methanol and methanol/water mixtures under air.
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