Pierre Fablet, Maria Dolores Fernandez-Martinez, Anke Spannenberg, Haijun Jiao, Ralf Jackstell, Matthias Beller
{"title":"Highly (regio)selective hydroformylation of olefins using self-assembling phosphines.","authors":"Pierre Fablet, Maria Dolores Fernandez-Martinez, Anke Spannenberg, Haijun Jiao, Ralf Jackstell, Matthias Beller","doi":"10.1039/d4ob00714j","DOIUrl":null,"url":null,"abstract":"<p><p>New phosphines with self-assembling 6-pyridinone moities were prepared, characterized, and examined in the hydroformylation of diverse olefins. Testing various known and novel ligands in the presence of [Rh(acac)(CO)<sub>2</sub>] under industrially relevant conditions, the hydroformylation of 1-octene proceeds best with 6,6'-(phenylphosphanediyl)bis(pyridin-2(1<i>H</i>)-one) (DPONP). Control experiments and modelling studies indicate dimerization of this ligand at higher temperatures (>100 °C). The optimal catalyst system is able to conserve high product linearity (>90%) for a broad range of olefins at industrially-employed temperatures at low ligand loading.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob00714j","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
New phosphines with self-assembling 6-pyridinone moities were prepared, characterized, and examined in the hydroformylation of diverse olefins. Testing various known and novel ligands in the presence of [Rh(acac)(CO)2] under industrially relevant conditions, the hydroformylation of 1-octene proceeds best with 6,6'-(phenylphosphanediyl)bis(pyridin-2(1H)-one) (DPONP). Control experiments and modelling studies indicate dimerization of this ligand at higher temperatures (>100 °C). The optimal catalyst system is able to conserve high product linearity (>90%) for a broad range of olefins at industrially-employed temperatures at low ligand loading.