Chemoselective Hydrogenation of Alkynes to (Z)-Alkenes Using an Air-Stable Base Metal Catalyst

被引:34
作者
Zubar, Viktoriia [1 ,2 ]
Sklyaruk, Jan [2 ]
Brzozowska, Aleksandra [2 ]
Rueping, Magnus [1 ]
机构
[1] KAUST, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia
[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
HOMOGENEOUS HYDROGENATION; SELECTIVE HYDROGENATION; MANGANESE COMPLEXES; SEMIHYDROGENATION; LIGANDS; ACTIVATION; EFFICIENT; KETONES; BOND; PD;
D O I
10.1021/acs.orglett.0c01783
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperativity.
引用
收藏
页码:5423 / 5428
页数:6
相关论文
共 75 条
[1]  
[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
[2]   Preparation and molecular and electronic structures of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilation [J].
Bart, SC ;
Lobkovsky, E ;
Chirik, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13794-13807
[3]   Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation [J].
Borghs, Jannik C. ;
Zubar, Viktoriia ;
Azofra, Luis Miguel ;
Sklyaruk, Jan ;
Rueping, Magnus .
ORGANIC LETTERS, 2020, 22 (11) :4222-4227
[4]   Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis [J].
Borghs, Jannik C. ;
Mai Anh Tran ;
Sklyaruk, Jan ;
Rueping, Magnus ;
El-Sepelgy, Osama .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :7927-7935
[5]   Manganese-Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation [J].
Borghs, Jannik C. ;
Azofra, Luis Miguel ;
Biberger, Tobias ;
Linnenberg, Oliver ;
Cavallo, Luigi ;
Rueping, Magnus ;
El-Sepelgy, Osama .
CHEMSUSCHEM, 2019, 12 (13) :3083-3088
[6]   Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines [J].
Borghs, Jannik C. ;
Lebedev, Yury ;
Rueping, Magnus ;
El-Sepelgy, Osama .
ORGANIC LETTERS, 2019, 21 (01) :70-74
[7]   Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
ORGANIC LETTERS, 2017, 19 (13) :3656-3659
[8]   Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst [J].
Brzozowska, Aleksandra ;
Zubar, Viktoriia ;
Ganardi, Ruth-Christine ;
Rueping, Magnus .
ORGANIC LETTERS, 2020, 22 (10) :3765-3769
[9]   Highly Chemo- and Stereoselective Transfer Semihydrogenation of Alkynes Catalyzed by a Stable, Well-Defined Manganese(II) Complex [J].
Brzozowska, Aleksandra ;
Azofra, Luis Miguel ;
Zubar, Viktoriia ;
Atodiresei, Iuliana ;
Cavallo, Luigi ;
Rueping, Magnus ;
El-Sepelgy, Osama .
ACS CATALYSIS, 2018, 8 (05) :4103-4109
[10]  
Bullock R. M., 2010, Catalysis without Precious Metals, V1