121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-384
Subject Rh(I)-Catalyzed Hydroformylation of Substituted Olefins Using Bicyclic Bridgehead Phosphoramidite Ligands
Authors Taeil Shin, Kim Hyunwoo*
Department of Chemistry, Korea Advanced Institute of Science and Technology, Korea
Abstract Hydroformylation is one of the powerful tools to make industrially and chemically useful aldehyde using Olefins as substrate and carbon monoxide and hydrogen gas in the presence of a metal catalyst. Also it is one way to increase one carbon in the olefin and the product aldehyde is itself valuable and can be converted to useful materials such as alcohol or amine via chemical conversion.1 Over the last few decades, many research has been reported on the hydroformylation reaction for mono- or disubstituted alkenes. On the other hand, the reaction of hydroformylation to high substituted olefins such as trisubstituted alkenes has not been reported. Because hydroformylation of trisubstituted alkene is proceeded in inefficient catalyst or condition. For example, high pressure and temperature need for this reaction and hard to selectivity control of linear and isomerization aldehyde.2,3,4 Here in, we performed rhodium catalyzed hydroformylation of trisubstituted alkenes by using bicyclic bridgehead phosphoramidite ligands, which is made by our group. Our briphos(bicyclic bridgehead phosphoramidite) ligands have an advantage of easily tunable properties such as elecitric and steric effects, and also show good reactivity and linear aldehyde selectivity in hydroformylation of trisubstituted alkenes. In the case of briphos ligands, it show much better reactivity and selectivity than other comercially available ligands. Among the various briphos ligands, especially, tBubriphos(3,5-MeOPh) ligand shows best reactivity and selectivity for the hydrofmylation of trisubstituted alkenes on various substrate. In addition, tBubriphos(3,5-MeOPh) ligand is resistant to functional groups in the substrate during this reaction.
E-mail tlsxodlf0453@kaist.ac.kr