Highly Selective Electrocatalytic Oxidation of Amines to Nitriles Assisted by Water Oxidation on Metal-Doped α-Ni(OH) 2

Sun, Yuxia; Shin, Hyeyoung; Wang, Fangyuan; Tian, Bailin; Chiang, Chen-Wei; Liu, Shengtang; Li, Xiaoshan; Wang, Yiqi; Tang, Lingyu; Goddard, William A.; Ding, Mengning

doi:10.1021/jacs.2c05403

Highly Selective Electrocatalytic Oxidation of Amines to Nitriles Assisted by Water Oxidation on Metal-Doped α-Ni(OH) ₂

Journal Article · 10 August 2022 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c05403· OSTI ID:1978496

Sun, Yuxia ^[1]; ^[2]; Wang, Fangyuan ^[1]; Tian, Bailin ^[1]; Chiang, Chen-Wei ^[1]; Liu, Shengtang ^[1]; Li, Xiaoshan ^[1]; Wang, Yiqi ^[1]; Tang, Lingyu ^[1]; ^[3]; ^[1]

Key Laboratory of Mesoscopic Chemistry, State Key Laboratory of Analytical Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
Graduate School of Energy Science and Technology (GEST), Chungnam National University, Daejeon 34134, Republic of Korea
Materials and Process Simulation Center (MSC) and Liquid Sunlight Alliance (LiSA), California Institute of Technology, Pasadena, California 91125, United States

Not provided.

Research Organization:: California Institute of Technology (CalTech), Pasadena, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0021266

OSTI ID:: 1978496

Journal Information:: Journal of the American Chemical Society, Vol. 144, Issue 33; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (46)

“Nanorust”-catalyzed Benign Oxidation of Amines for Selective Synthesis of Nitriles Jagadeesh, Rajenahally V.; Junge, Henrik; Beller, Matthias ChemSusChem, Vol. 8, Issue 1 https://doi.org/10.1002/cssc.201402613	journal	October 2014
Copper(II)‐Catalyzed Aerobic Oxidation of Amines: Divergent Reaction Pathways by Solvent Control to Imines and Nitriles Kim, Jihyeon; Golime, Gangadhararao; Kim, Hun Young Asian Journal of Organic Chemistry, Vol. 8, Issue 9 https://doi.org/10.1002/ajoc.201900302	journal	July 2019
Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion Xu, Boran; Hartigan, Elizabeth M.; Feula, Giancarlo Angewandte Chemie International Edition, Vol. 55, Issue 51 https://doi.org/10.1002/anie.201609255	journal	November 2016
Efficient Heterogeneous Aerobic Oxidation of Amines by a Supported Ruthenium Catalyst Yamaguchi, Kazuya; Mizuno, Noritaka Angewandte Chemie International Edition, Vol. 42, Issue 13 https://doi.org/10.1002/anie.200250779	journal	April 2003
Visible-Light-Driven Aerobic Oxidation of Amines to Nitriles over Hydrous Ruthenium Oxide Supported on TiO ₂ Ovoshchnikov, Daniil S.; Donoeva, Baira G.; Golovko, Vladimir B. ACS Catalysis, Vol. 5, Issue 1 https://doi.org/10.1021/cs501186n	journal	November 2014
Photocatalytic selective aerobic oxidation of amines to nitriles over Ru/γ-Al₂O₃: the role of the support surface and the strong imine intermediate adsorption Zhu, Pengqi; Zhang, Jin; Wang, Jie Catalysis Science & Technology, Vol. 10, Issue 2 https://doi.org/10.1039/c9cy01916b	journal	January 2020
Organic Electrosynthesis: From Laboratorial Practice to Industrial Applications Cardoso, David S. P.; Šljukić, Biljana; Santos, Diogo M. F. Organic Process Research & Development, Vol. 21, Issue 9 https://doi.org/10.1021/acs.oprd.7b00004	journal	August 2017
Organic electrosynthesis: a promising green methodology in organic chemistry Frontana-Uribe, Bernardo A.; Little, R. Daniel; Ibanez, Jorge G. Green Chemistry, Vol. 12, Issue 12 https://doi.org/10.1039/c0gc00382d	journal	January 2010
Defect engineering of nickel hydroxide nanosheets by Ostwald ripening for enhanced selective electrocatalytic alcohol oxidation Chen, Xianlang; Zhong, Xing; Yuan, Bowen Green Chemistry, Vol. 21, Issue 3 https://doi.org/10.1039/c8gc03451f	journal	January 2019
Ultrastable and efficient H₂ production via membrane-free hybrid water electrolysis over a bifunctional catalyst of hierarchical Mo–Ni alloy nanoparticles Cui, Xin; Chen, Meiling; Xiong, Rui Journal of Materials Chemistry A, Vol. 7, Issue 27 https://doi.org/10.1039/c9ta03924d	journal	January 2019
Integrating Hydrogen Production with Aqueous Selective Semi‐Dehydrogenation of Tetrahydroisoquinolines over a Ni ₂ P Bifunctional Electrode Huang, Chenqi; Huang, Yi; Liu, Cuibo Angewandte Chemie International Edition, Vol. 58, Issue 35 https://doi.org/10.1002/anie.201903327	journal	August 2019
Paired Electrochemical Reactions and the On-Site Generation of a Chemical Reagent Wu, Tiandi; Nguyen, Bichlien H.; Daugherty, Michael C. Angewandte Chemie International Edition, Vol. 58, Issue 11 https://doi.org/10.1002/anie.201900343	journal	February 2019
Boosting Hydrogen Production by Anodic Oxidation of Primary Amines over a NiSe Nanorod Electrode Huang, Yi; Chong, Xiaodan; Liu, Cuibo Angewandte Chemie International Edition, Vol. 57, Issue 40 https://doi.org/10.1002/anie.201807717	journal	October 2018
Simultaneous H ₂ Generation and Biomass Upgrading in Water by an Efficient Noble-Metal-Free Bifunctional Electrocatalyst You, Bo; Jiang, Nan; Liu, Xuan Angewandte Chemie International Edition, Vol. 55, Issue 34 https://doi.org/10.1002/anie.201603798	journal	July 2016
Vacancy‐Rich Ni(OH) ₂ Drives the Electrooxidation of Amino C−N Bonds to Nitrile C≡N Bonds Wang, Wenbin; Wang, Yutang; Yang, Ruoou Angewandte Chemie International Edition, Vol. 59, Issue 39 https://doi.org/10.1002/anie.202005574	journal	July 2020
Highly selective electrocatalytic oxidation of benzyl C–H using water as safe and sustainable oxygen source Sun, Yuxia; Li, Xiaoshan; Yang, Miao Green Chemistry, Vol. 22, Issue 21 https://doi.org/10.1039/d0gc01871f	journal	January 2020
Selective Activation of Propane Using Intermediates Generated during Water Oxidation Zhang, Haochen; Li, Chunsong; Lu, Qi Journal of the American Chemical Society, Vol. 143, Issue 10 https://doi.org/10.1021/jacs.1c00377	journal	March 2021
2D Layered Double Hydroxides for Oxygen Evolution Reaction: From Fundamental Design to Application Lv, Lin; Yang, Zhaoxi; Chen, Kun Advanced Energy Materials, Vol. 9, Issue 17 https://doi.org/10.1002/aenm.201803358	journal	March 2019
Recent advances in energy chemistry of precious-metal-free catalysts for oxygen electrocatalysis Wang, Bin; Cui, Xiaoyang; Huang, Jiaqi Chinese Chemical Letters, Vol. 29, Issue 12 https://doi.org/10.1016/j.cclet.2018.11.021	journal	December 2018
Oriented Transformation of Co‐LDH into 2D/3D ZIF‐67 to Achieve Co–N–C Hybrids for Efficient Overall Water Splitting Chen, Ziliang; Ha, Yuan; Jia, Huaxian Advanced Energy Materials, Vol. 9, Issue 19 https://doi.org/10.1002/aenm.201803918	journal	March 2019
Effects of Intentionally Incorporated Metal Cations on the Oxygen Evolution Electrocatalytic Activity of Nickel (Oxy)hydroxide in Alkaline Media Enman, Lisa J.; Burke, Michaela S.; Batchellor, Adam S. ACS Catalysis, Vol. 6, Issue 4 https://doi.org/10.1021/acscatal.5b02924	journal	March 2016
Efficient Water Oxidation Using Nanostructured α-Nickel-Hydroxide as an Electrocatalyst Gao, Minrui; Sheng, Wenchao; Zhuang, Zhongbin Journal of the American Chemical Society, Vol. 136, Issue 19 https://doi.org/10.1021/ja502128j	journal	May 2014
Precipitating Metal Nitrate Deposition of Amorphous Metal Oxyhydroxide Electrodes Containing Ni, Fe, and Co for Electrocatalytic Water Oxidation Kim, Young Kyeong; Kim, Jin Hyun; Jo, Yim Hyun ACS Catalysis, Vol. 9, Issue 10 https://doi.org/10.1021/acscatal.9b02701	journal	September 2019
Ultrathin Cobalt–Manganese Layered Double Hydroxide Is an Efficient Oxygen Evolution Catalyst Song, Fang; Hu, Xile Journal of the American Chemical Society, Vol. 136, Issue 47 https://doi.org/10.1021/ja5096733	journal	November 2014
Unraveling Two Pathways for Electrochemical Alcohol and Aldehyde Oxidation on NiOOH Bender, Michael T.; Lam, Yan Choi; Hammes-Schiffer, Sharon Journal of the American Chemical Society, Vol. 142, Issue 51 https://doi.org/10.1021/jacs.0c10924	journal	December 2020
Tuning OH binding energy enables selective electrochemical oxidation of ethylene to ethylene glycol Lum, Yanwei; Huang, Jianan Erick; Wang, Ziyun Nature Catalysis, Vol. 3, Issue 1 https://doi.org/10.1038/s41929-019-0386-4	journal	January 2020
Double‐Exchange‐Induced in situ Conductivity in Nickel‐Based Oxyhydroxides: An Effective Descriptor for Electrocatalytic Oxygen Evolution Tian, Bailin; Shin, Hyeyoung; Liu, Shengtang Angewandte Chemie International Edition, Vol. 60, Issue 30 https://doi.org/10.1002/anie.202101906	journal	June 2021
Mo- and Fe-Modified Ni(OH) ₂ /NiOOH Nanosheets as Highly Active and Stable Electrocatalysts for Oxygen Evolution Reaction Jin, Yanshuo; Huang, Shangli; Yue, Xin ACS Catalysis, Vol. 8, Issue 3 https://doi.org/10.1021/acscatal.7b04226	journal	January 2018
A General Method to Probe Oxygen Evolution Intermediates at Operating Conditions Tao, Hua Bing; Xu, Yinghua; Huang, Xiang Joule, Vol. 3, Issue 6 https://doi.org/10.1016/j.joule.2019.03.012	journal	June 2019
Porous Multishelled Ni ₂ P Hollow Microspheres as an Active Electrocatalyst for Hydrogen and Oxygen Evolution Sun, Hongming; Xu, Xiaobin; Yan, Zhenhua Chemistry of Materials, Vol. 29, Issue 19 https://doi.org/10.1021/acs.chemmater.7b03627	journal	October 2017
Oxygen Isotope Labeling Experiments Reveal Different Reaction Sites for the Oxygen Evolution Reaction on Nickel and Nickel Iron Oxides Lee, Seunghwa; Banjac, Karla; Lingenfelder, Magalí Angewandte Chemie International Edition, Vol. 58, Issue 30 https://doi.org/10.1002/anie.201903200	journal	July 2019
An Investigation of Thin-Film Ni–Fe Oxide Catalysts for the Electrochemical Evolution of Oxygen Louie, Mary W.; Bell, Alexis T. Journal of the American Chemical Society, Vol. 135, Issue 33 https://doi.org/10.1021/ja405351s	journal	August 2013
In Situ Observation of Active Oxygen Species in Fe-Containing Ni-Based Oxygen Evolution Catalysts: The Effect of pH on Electrochemical Activity Trześniewski, Bartek J.; Diaz-Morales, Oscar; Vermaas, David A. Journal of the American Chemical Society, Vol. 137, Issue 48 https://doi.org/10.1021/jacs.5b06814	journal	November 2015
Activity Origins and Design Principles of Nickel-Based Catalysts for Nucleophile Electrooxidation Chen, Wei; Xie, Chao; Wang, Yanyong Chem, Vol. 6, Issue 11 https://doi.org/10.1016/j.chempr.2020.07.022	journal	November 2020
Fabrication of hierarchical hollow Mn doped Ni(OH)2 nanostructures with enhanced catalytic activity towards electrochemical oxidation of methanol Dong, Bing; Li, Wei; Huang, Xiaoxiao Nano Energy, Vol. 55 https://doi.org/10.1016/j.nanoen.2018.10.050	journal	January 2019
Encapsulate α-MnO2 nanofiber within graphene layer to tune surface electronic structure for efficient ozone decomposition Zhu, Guoxiang; Zhu, Wei; Lou, Yang Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-24424-x	journal	July 2021
Quantitative analysis of Ni2+/Ni3+ in Li[NixMnyCoz]O2 cathode materials: Non-linear least-squares fitting of XPS spectra Fu, Zewei; Hu, Juntao; Hu, Wenlong Applied Surface Science, Vol. 441 https://doi.org/10.1016/j.apsusc.2018.02.114	journal	May 2018
Operando Identification of the Dynamic Behavior of Oxygen Vacancy-Rich Co ₃ O ₄ for Oxygen Evolution Reaction Xiao, Zhaohui; Huang, Yu-Cheng; Dong, Chung-Li Journal of the American Chemical Society, Vol. 142, Issue 28 https://doi.org/10.1021/jacs.0c00257	journal	June 2020
Selective Electrooxidation of Biomass‐Derived Alcohols to Aldehydes in a Neutral Medium: Promoted Water Dissociation over a Nickel‐Oxide‐Supported Ruthenium Single‐Atom Catalyst Ge, Ruixiang; Wang, Ye; Li, Zezhou Angewandte Chemie International Edition, Vol. 61, Issue 19 https://doi.org/10.1002/anie.202200211	journal	February 2022
The significance of electrochemical impedance spectra recorded during active oxygen evolution for oxide covered Ni, Co and Fe electrodes in alkaline solution Lyons, Michael E. G.; Brandon, Michael P. Journal of Electroanalytical Chemistry, Vol. 631, Issue 1-2 https://doi.org/10.1016/j.jelechem.2009.03.019	journal	June 2009
Mechanistic Studies of the Oxygen Evolution Reaction Mediated by a Nickel–Borate Thin Film Electrocatalyst Bediako, D. Kwabena; Surendranath, Yogesh; Nocera, Daniel G. Journal of the American Chemical Society, Vol. 135, Issue 9 https://doi.org/10.1021/ja3126432	journal	February 2013
Epoxidation of Cyclooctene Using Water as the Oxygen Atom Source at Manganese Oxide Electrocatalysts Jin, Kyoungsuk; Maalouf, Joseph H.; Lazouski, Nikifar Journal of the American Chemical Society, Vol. 141, Issue 15 https://doi.org/10.1021/jacs.9b02345	journal	March 2019
In Silico Discovery of New Dopants for Fe-Doped Ni Oxyhydroxide (Ni _{1– x} Fe _x OOH) Catalysts for Oxygen Evolution Reaction Shin, Hyeyoung; Xiao, Hai; Goddard, William A. Journal of the American Chemical Society, Vol. 140, Issue 22 https://doi.org/10.1021/jacs.8b02225	journal	April 2018
Synergy between Fe and Ni in the optimal performance of (Ni,Fe)OOH catalysts for the oxygen evolution reaction Xiao, Hai; Shin, Hyeyoung; Goddard, William A. Proceedings of the National Academy of Sciences, Vol. 115, Issue 23 https://doi.org/10.1073/pnas.1722034115	journal	May 2018
Alcohols electrooxidation coupled with H2 production at high current densities promoted by a cooperative catalyst Li, Zhenhua; Yan, Yifan; Xu, Si-Min Nature Communications, Vol. 13, Issue 1 https://doi.org/10.1038/s41467-021-27806-3	journal	January 2022
Nanotechnology makes biomass electrolysis more energy efficient than water electrolysis Chen, Y. X.; Lavacchi, A.; Miller, H. A. Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms5036	journal	June 2014

Similar Records

Single-Site Cobalt Catalysts at New Zr₁₂(μ ₃ -O)₈(μ₃-OH) ₈(μ ₂ -OH)₆ Metal–Organic Framework Nodes for Highly Active Hydrogenation of Nitroarenes, Nitriles, and Isocyanides

Journal Article · 2017 · Journal of the American Chemical Society · OSTI ID:1373786

Ji, Pengfei; Manna, Kuntal; Lin, Zekai; +4 more

Doping palladium with tellurium for the highly selective electrocatalytic reduction of aqueous CO₂ to CO

Journal Article · 2017 · Chemical Science (Online) · OSTI ID:1719125

Tao, Hengcong; Sun, Xiaofu; Back, Seoin; +8 more

Highly selective electrocatalytic CO₂ reduction to ethanol by metallic clusters dynamically formed from atomically dispersed copper

Journal Article · 2020 · Nature Energy · OSTI ID:1671779

Xu, Haiping; Rebollar, Dominic; He, Haiying; +9 more

Related Subjects

Chemistry

Highly Selective Electrocatalytic Oxidation of Amines to Nitriles Assisted by Water Oxidation on Metal-Doped α-Ni(OH) 2

Citation Formats

References (46)

Similar Records

Related Subjects

Highly Selective Electrocatalytic Oxidation of Amines to Nitriles Assisted by Water Oxidation on Metal-Doped α-Ni(OH) ₂