The history and future challenges associated with the hydrogenation of vinyl fluorides

被引:19
作者
Sedgwick, Daniel M. [1 ,2 ,3 ]
Hammond, Gerald B. [1 ]
机构
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
[2] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
[3] Ctr Invest Principe Felipe, Lab Mol Organ, Valencia 46012, Spain
基金
美国国家科学基金会;
关键词
Vinyl fluoride; Fluoroalkene; Catalytic hydrogenation; Palladium; Iridium; Rhodium; CATALYZED ASYMMETRIC HYDROGENATION; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE HYDROGENATION; AMINO-ACIDS; COMPLEXES; OLEFINS; ACCESS; BOND; HYDRODEFLUORINATION; HYDROGENOLYSIS;
D O I
10.1016/j.jfluchem.2017.12.019
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Catalytic hydrogenation is one of the most powerful transformations available in synthetic chemistry; there have been three Nobel Laureates rewarded for their work in the field. Despite the advances in substrate scope and the development of enantioselective versions of this transformation, vinyl fluorides remain somewhat under-represented. Successful hydrogenation of vinyl fluorides can give rise to a fluorine-containing stereocenter, an important feature which has great potential in many areas of chemistry. This review aims to explore the history of vinyl fluorides as substrates in hydrogenation reactions, and to highlight modern day challenges and unresolved issues regarding this ambitious transformation.
引用
收藏
页码:45 / 58
页数:14
相关论文
共 56 条
[31]   The hydrogenation of beta-hydroxy-gamma-fluoro-gamma-ethylenic esters as an efficient approach to the fluorohydrin substructure [J].
LucetLevannier, K ;
Lellouche, JP ;
Mioskowski, C ;
Schneider, F ;
Cassagne, C .
TETRAHEDRON LETTERS, 1996, 37 (12) :2007-2010
[32]   Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1′-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators [J].
McCune, Christopher D. ;
Beio, Matthew L. ;
Sturdivant, Jill M. ;
de la Salud-Bea, Roberto ;
Darnell, Brendan M. ;
Berkowitz, David B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (40) :14077-14089
[33]   Fluoroolefins as Peptidie Mimetics. 2. A Computational Study of the Conformational Ramifications of Peptide Bond Replacement [J].
McKinney, Brian E. ;
Urban, Joseph J. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2010, 114 (02) :1123-1133
[34]  
NELSON TD, 2006, Patent No. 2006069287
[35]  
Noveski D., 2003, DALT T, V6, P4075
[36]  
Noyori R, 2002, ANGEW CHEM INT EDIT, V41, P2008, DOI 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO
[37]  
2-4
[38]   ASYMMETRIC HYDROGENATION OF UNSATURATED CARBOXYLIC-ACIDS CATALYZED BY BINAP-RUTHENIUM(II) COMPLEXES [J].
OHTA, T ;
TAKAYA, H ;
KITAMURA, M ;
NAGAI, K ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3174-3176
[39]   PREPARATION AND PROPERTIES OF TRIS(TRIPHENYLPHOSPHINE)HALOGENORHODIUM(1) AND SOME REACTIONS THEREOF INCLUDING CATALYTIC HOMOGENEOUS HYDROGENATION OF OLEFINS AND ACETYLENES AND THEIR DERIVATIVES [J].
OSBORN, JA ;
JARDINE, FH ;
YOUNG, JF ;
WILKINSO.G .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1966, (12) :1711-&
[40]   Synthesis of 2′,3′-dideoxy-2′-monofluoromethyI azanucleosides [J].
Qiu, XL ;
Qing, FL .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) :277-283