Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2 as Sole Reductant

被引:18
作者
Zhou, Xibing [1 ,2 ]
Zhang, Guoying [3 ]
Huang, Renbin [1 ,2 ]
Huang, Hanmin [1 ,2 ,3 ,4 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[4] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
CHIRAL DIPHOSPHINE LIGANDS; ALKYL-HALIDES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ARYL BROMIDES; COMPLEXES; HYDROGENOLYSIS; HYDROGENATION; ALDEHYDES; ELIMINATION;
D O I
10.1021/acs.orglett.0c03865
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H-2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H-2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.
引用
收藏
页码:365 / 369
页数:5
相关论文
共 71 条
[1]   Cobalt-catalyzed vinylation of functionalized aryl halides with vinyl acetates [J].
Amatore, M ;
Gosmini, C ;
Périchon, J .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (06) :989-992
[2]   Synthesis of functionalised diarylmethanes via a cobalt-catalysed cross-coupling of arylzinc species with benzyl chlorides [J].
Amatore, Muriel ;
Gosmini, Corinne .
CHEMICAL COMMUNICATIONS, 2008, (40) :5019-5021
[3]   Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate [J].
Amatore, Muriel ;
Gosmini, Corinne .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2089-2092
[4]   Reductive coupling of terpenic allylic halides catalyzed by CP2TiCl:: A short and efficient asymmetric synthesis of onocerane triterpenes [J].
Barrero, AF ;
Herrador, MM ;
del Moral, JFQ ;
Arteaga, P ;
Arteaga, JF ;
Piedra, M ;
Sánchez, EM .
ORGANIC LETTERS, 2005, 7 (12) :2301-2304
[5]   Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides:: Efficient synthesis of symmetric terpenes [J].
Barrero, Alejandro F. ;
Mar Herrador, M. ;
Quilez del Moral, Jose F. ;
Arteaga, Pilar ;
Arteaga, Jesus F. ;
Dieguez, Horacio R. ;
Sanchez, Elena M. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :2988-2995
[6]   Hydrogenation, hydrogenolysis, and desulfurization of thiophenes by soluble metal complexes: Recent achievements and future directions [J].
Bianchini, C ;
Meli, A .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (03) :109-116
[7]   Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].
Biswas, Soumik ;
Weix, Daniel J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197
[8]  
Brown RCD, 2001, ANGEW CHEM INT EDIT, V40, P4496, DOI 10.1002/1521-3773(20011203)40:23<4496::AID-ANIE4496>3.0.CO
[9]  
2-F
[10]   Diastereocontrol in Asymmetric Allyl-Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides [J].
Brozek, Laura A. ;
Ardolino, Michael J. ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) :16778-16781