Work

Efficient Ring Closing Metathesis by NHC-Supported (Arylimido)vanadium(V)-Alkylidene Catalysts Containing Perhalophenoxide Ligands: Exclusive RCM under High Substrate Concentration

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Ring closing metathesis (RCM) reactions of N, N -diallyl-4-toluenesulfonamide ( S1 ) and N, N -diallylaniline ( S2 ) by V(N-2,6-Cl 2 C 6 H 3 )(CHSiMe 3 )(OC 6 X 5 )(NHC) [X = F, Cl ( 4 ), Br ( 5 ); NHC = 1,3-bis(2,6-dimethylphenyl)imidazole-2-ylidene (IXy)] exclusively afforded the corresponding ring closed products (yields 83 to >99%) under high initial substrate concentration conditions (3.2–24 M). A significant increase in the activity was observed upon increasing the substrate concentrations, leading to highly efficient RCM [RCM of S2 by 4, 5: TON = >1000, TOF = >100 s –1, yield (conv.) 95 to >99%]. The RCM of diallyl ether and diallyl thioether afforded the corresponding ring closed products exclusively, whereas the activities increased with dilution of the substrate concentrations. The RCM of 1,7-octadiene also gave cyclohexene.

Source: Organometallics

DOI: 10.1021/acs.organomet.5c00224

Authors: Jirapa Suthala, Moe Unoki, Michael R. Buchmeiser, Kotohiro Nomura

Institutions: Tokyo Metropolitan University, University of Stuttgart, Deutschen Institute für Textil und Faserforschung

Language: English

Topic: Synthetic Organic Chemistry Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Deutsche Forschungsgemeinschaft, Japan Society for the Promotion of Science