Electrocatalytic asymmetric hydrogenation of α,β-unsaturated acids in a PEM reactor with cinchona-modified palladium catalysts

被引：19

作者：

Fukazawa, Atsushi ^{[1
]}

Tanaka, Kenta ^{[1
]}

Hashimoto, Yasushi ^{[2
]}

Sato, Yasushi ^{[2
]}

Atobe, Mahito ^{[1
]}

机构：

[1] Yokohama Natl Univ, Grad Sch Sci & Engn, Hodogaya Ku, 79-1 Tokiwadai, Yokohama, Kanagawa 2408501, Japan

[2] NXTG Nippon Oil & Energy Co, R&D Solut Ctr, Naka Ku, 8 Chidoricho, Yokohama, Kanagawa 2310815, Japan

来源：

ELECTROCHEMISTRY COMMUNICATIONS | 2020年 / 115卷

关键词：

Electrosynthesis; Proton-exchange membrane (PEM) reactor; Electrocatalytic asymmetric hydrogenation; alpha; beta-Unsaturated acids; Cinchona-modified palladium catalysts; ENANTIOSELECTIVE HYDROGENATION; ORGANIC ELECTROCHEMISTRY; ADSORPTION; REDUCTION; OXIDATION; PLATINUM; PROGRESS; ALKYNES;

D O I：

10.1016/j.elecom.2020.106734

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

We have developed an electrocatalytic asymmetric hydrogenation reaction using a proton-exchange membrane (PEM) reactor that employs a polymer electrolyte fuel cell and industrial electrolysis technologies. Reasonable enantioselectivities and excellent current efficiencies were obtained in the asymmetric hydrogenation of alpha-phenylcinnamic acid under mild conditions without adding a supporting electrolyte. The current density was crucial to achieving the improved results observed.

引用

页数：5

共 39 条

[1] STEREOCHEMICAL STUDIES OF THE ELECTROLYTIC REACTIONS OF ORGANIC-COMPOUNDS .19. ELECTROORGANIC REACTIONS ON ORGANIC ELECTRODES .1. ASYMMETRIC REDUCTION OF PROCHIRAL ACTIVATED OLEFINS ON A POLY-L-VALINE-COATED GRAPHITE
ABE, S
NONAKA, T
FUCHIGAMI, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) : 3630 - 3632
[2] Synthesis, Characterization, and Electrochemical Applications of Chiral Imprinted Mesoporous Ni Surfaces
Assavapanumat, Sunpet
Ketkaew, Marisa
Kuhn, Alexander
Wattanakit, Chularat
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (47) : 18870 - 18876
[3] The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: A combined electrochemical - STM approach
Attard, GA
Ahmadi, A
Jenkins, DJ
Hazzazi, OA
Wells, PB
Griffin, KG
Johnston, P
Gillies, JE
[J]. CHEMPHYSCHEM, 2003, 4 (02) : 123 - 130
[4] Progress in enantioselective catalysis assessed from an industrial point of view
Blaser, HU
Pugin, B
Spindler, F
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 231 (1-2) : 1 - 20
[5] A mixed-ligand approach enables the asymmetric hydrogenation of an α-isopropylcinnamic acid en route to the renin inhibitor aliskiren
Boogers, Jeroen A. F.
Felfer, Ulfried
Kotthaus, Martina
Lefort, Laurent
Steinbauer, Gerhard
de Vries, Andre H. M.
de Vries, Johannes G.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) : 585 - 591
[6] ADSORPTION BEHAVIOUR OF QUINOLINE 2- AND 4-METHYLQUINOLINE AT MERCURY-SOLUTION AND AT AIR-SOLUTION INTERFACES .I. ELECTROCAPILLARY CURVES SURFACE TENSION AND SURFACE POTENTIAL
BORDI, S
PAPESCHI, G
[J]. JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1969, 20 (02): : 297 - &
[7] Industrial methods for the production of optically active intermediates
Breuer, M
Ditrich, K
Habicher, T
Hauer, B
Kesseler, M
Stürmer, R
Zelinski, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) : 788 - 824
[8] A comprehensive review on PEM water electrolysis
Carmo, Marcelo
Fritz, David L.
Merge, Juergen
Stolten, Detlef
[J]. INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2013, 38 (12) : 4901 - 4934
[9] Perspectives in Flow Electrochemistry
Folgueiras-Amador, Ana A.
Wirth, Thomas
[J]. JOURNAL OF FLOW CHEMISTRY, 2017, 7 (3-4) : 94 - 95
[10] Nickel-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Alkynes with Formic Acid through Catalytic CO Recycling
Fu, Ming-Chen
Shang, Rui
Cheng, Wan-Min
Fu, Yao
[J]. ACS CATALYSIS, 2016, 6 (04): : 2501 - 2505

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