Catalytic asymmetric hydrogenation using a [2.2]paracyclophane based chiral 1,2,3-triazol-5-ylidene-Pd complex under ambient conditions and 1 atmosphere of H2

被引:36
作者
Dasgupta, Ayan [1 ]
Ramkumar, Venkatachalam [1 ]
Sankararaman, Sethuraman [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India
关键词
N-HETEROCYCLIC CARBENES; PALLADIUM COMPLEXES; LIGANDS SYNTHESIS; PLANAR; 1,2,3-TRIAZOLYLIDENES; PHOSPHINE;
D O I
10.1039/c5ra03021h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral 1,2,3-triazol-5-ylidene-Pd complexes with the planar chiral [2.2]paracyclophane wing tip group have been synthesized and structurally characterized. The complex with a labile acetonitrile co-ligand is an excellent catalyst for chemoselective hydrogenation of alkynes and alkenes and enantioselective hydrogenation of prochiral alkenes at ambient conditions and 1.0 atmosphere of H-2.
引用
收藏
页码:21558 / 21561
页数:4
相关论文
共 48 条
[1]   [2.2]Paracyclophane-Triazolyl Monophosphane Ligands: Synthesis and Their Copper and Palladium Complexes [J].
Austeri, Martina ;
Enders, Mirja ;
Nieger, Martin ;
Braese, Stefan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (09) :1667-1670
[2]   Planar and central chiral [2.2]paracyclophanes as powerful catalysts for asymmetric 1,2-addition reactions [J].
Bräse, S ;
Dahmen, S ;
Höfener, S ;
Lauterwasser, F ;
Kreis, M ;
Ziegert, RE .
SYNLETT, 2004, (15) :2647-2669
[3]  
Campbell CD, 2011, CATAL MET COMPLEXES, V32, P263, DOI 10.1007/978-90-481-2866-2_12
[4]   Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].
César, V ;
Bellemin-Laponnaz, S ;
Gade, LH .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636
[5]   First chelated chiral N-Heterocyclic bis-carbene complexes [J].
Clyne, DS ;
Jin, J ;
Genest, E ;
Gallucci, JC ;
RajanBabu, TV .
ORGANIC LETTERS, 2000, 2 (08) :1125-1128
[6]   Abnormal, mesoionic and remote N-heterocyclic carbene complexes [J].
Crabtree, Robert H. .
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (3-4) :755-766
[7]   1,3,4-Trisubstituted-1,2,3-Triazol-5-ylidene 'Click' Carbene Ligands: Synthesis, Catalysis and Self-Assembly [J].
Crowley, James D. ;
Lee, Ai-Lan ;
Kilpin, Kelly J. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (08) :1118-1132
[8]   Stereoelectronic parameters associated with N-heterocyclic carbene (NHC) ligands:: A quest for understanding [J].
Diez-Gonzalez, Silvia ;
Nolan, Steven P. .
COORDINATION CHEMISTRY REVIEWS, 2007, 251 (5-6) :874-883
[9]   N-Heterocyclic Carbenes in Late Transition Metal Catalysis [J].
Diez-Gonzalez, Silvia ;
Marion, Nicolas ;
Nolan, Steven P. .
CHEMICAL REVIEWS, 2009, 109 (08) :3612-3676
[10]   Application of 1,2,3-triazolylidenes as versatile NHC-type ligands: synthesis, properties, and application in catalysis and beyond [J].
Donnelly, Kate F. ;
Petronilho, Ana ;
Albrecht, Martin .
CHEMICAL COMMUNICATIONS, 2013, 49 (12) :1145-1159