Jirapa Suthala, Moe Unoki, Michael R. Buchmeiser* and Kotohiro Nomura*,
{"title":"含过卤代酚配体的nhc负载（芳基氨基）钒(V)-烷基基催化剂的高效合环复合反应：高底物浓度下的独占RCM","authors":"Jirapa Suthala, Moe Unoki, Michael R. Buchmeiser* and Kotohiro Nomura*, ","doi":"10.1021/acs.organomet.5c00224","DOIUrl":null,"url":null,"abstract":"<p >Ring closing metathesis (RCM) reactions of <i>N</i>,<i>N</i>-diallyl-4-toluenesulfonamide (<b>S1</b>) and <i>N</i>,<i>N</i>-diallylaniline (<b>S2</b>) by V(N-2,6-Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>)(CHSiMe<sub>3</sub>)(OC<sub>6</sub>X<sub>5</sub>)(NHC) [X = F, Cl (<b>4</b>), Br (<b>5</b>); 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 <b>S2</b> by <b>4</b>,<b>5</b>: TON = >1000, TOF = >100 s<sup>–1</sup>, 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.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 17","pages":"1870–1875"},"PeriodicalIF":2.9000,"publicationDate":"2025-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00224","citationCount":"0","resultStr":"{\"title\":\"Efficient Ring Closing Metathesis by NHC-Supported (Arylimido)vanadium(V)-Alkylidene Catalysts Containing Perhalophenoxide Ligands: Exclusive RCM under High Substrate Concentration\",\"authors\":\"Jirapa Suthala, Moe Unoki, Michael R. Buchmeiser* and Kotohiro Nomura*, \",\"doi\":\"10.1021/acs.organomet.5c00224\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Ring closing metathesis (RCM) reactions of <i>N</i>,<i>N</i>-diallyl-4-toluenesulfonamide (<b>S1</b>) and <i>N</i>,<i>N</i>-diallylaniline (<b>S2</b>) by V(N-2,6-Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>)(CHSiMe<sub>3</sub>)(OC<sub>6</sub>X<sub>5</sub>)(NHC) [X = F, Cl (<b>4</b>), Br (<b>5</b>); 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 <b>S2</b> by <b>4</b>,<b>5</b>: TON = >1000, TOF = >100 s<sup>–1</sup>, 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.</p>\",\"PeriodicalId\":56,\"journal\":{\"name\":\"Organometallics\",\"volume\":\"44 17\",\"pages\":\"1870–1875\"},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2025-08-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00224\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organometallics\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.organomet.5c00224\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organometallics","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.organomet.5c00224","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Efficient Ring Closing Metathesis by NHC-Supported (Arylimido)vanadium(V)-Alkylidene Catalysts Containing Perhalophenoxide Ligands: Exclusive RCM under High Substrate Concentration
Ring closing metathesis (RCM) reactions of N,N-diallyl-4-toluenesulfonamide (S1) and N,N-diallylaniline (S2) by V(N-2,6-Cl2C6H3)(CHSiMe3)(OC6X5)(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.
期刊介绍：
Organometallics is the flagship journal of organometallic chemistry and records progress in one of the most active fields of science, bridging organic and inorganic chemistry. The journal publishes Articles, Communications, Reviews, and Tutorials (instructional overviews) that depict research on the synthesis, structure, bonding, chemical reactivity, and reaction mechanisms for a variety of applications, including catalyst design and catalytic processes; main-group, transition-metal, and lanthanide and actinide metal chemistry; synthetic aspects of polymer science and materials science; and bioorganometallic chemistry.
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