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A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep and its application in asymmetric hydrogenation
Zhang, De-Yang1,2; Yu, Chang-Bin2; Wang, Min-Can1; Gao, Kai2; Zhou, Yong-Gui2
KeywordAsymmetric Catalysis Fluorinated Diphosphine Ligands Quinolines Indoles
Source PublicationTETRAHEDRON LETTERS
2012-05-16
DOI10.1016/j.tetlet.2012.03.036
Volume53Issue:20Pages:2556-2559
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordHIGHLY ENANTIOSELECTIVE HYDROGENATION ; IRIDIUM-CATALYZED HYDROGENATION ; HETEROAROMATIC-COMPOUNDS ; ARYLBORONIC ACIDS ; BISPHOSPHINE LIGANDS ; DIENE LIGANDS ; QUINOLINES ; 1,4-ADDITION ; INDOLES ; DIFLUORPHOS
AbstractA new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep was synthesized from 1-bromo-3-(trifluoromethoxy)benzene in high yield. The key steps included oxidative coupling with anhydrous ferric chloride and optical resolution by (+)-DMTA. The ligand afforded high performance for Ir-catalyzed asymmetric hydrogenation of quinolines with ee up to 92% and TON up to 25,000. It was also successfully applied to the Pd-catalyzed asymmetric hydrogenation of simple indoles with ee up to 87% and Rh-catalyzed asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone with 97% ee. (C) 2012 Elsevier Ltd. All rights reserved.
Language英语
WOS IDWOS:000303372200018
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Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/142978
Collection中国科学院大连化学物理研究所
Affiliation1.Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Henan, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
Recommended Citation
GB/T 7714
Zhang, De-Yang,Yu, Chang-Bin,Wang, Min-Can,et al. A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep and its application in asymmetric hydrogenation[J]. TETRAHEDRON LETTERS,2012,53(20):2556-2559.
APA Zhang, De-Yang,Yu, Chang-Bin,Wang, Min-Can,Gao, Kai,&Zhou, Yong-Gui.(2012).A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep and its application in asymmetric hydrogenation.TETRAHEDRON LETTERS,53(20),2556-2559.
MLA Zhang, De-Yang,et al."A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep and its application in asymmetric hydrogenation".TETRAHEDRON LETTERS 53.20(2012):2556-2559.
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