Zn-Nx sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds

被引:143
作者
Xie, Chao [1 ,2 ]
Lin, Longfei [3 ]
Huang, Liang [4 ]
Wang, Zixin [1 ,2 ]
Jiang, Zhiwei [1 ,2 ]
Zhang, Zehui [1 ,2 ]
Han, Buxing [3 ]
机构
[1] South Cent Univ Nationalities, Minist Educ, Key Lab Catalysis & Energy Mat Chem, Wuhan, Peoples R China
[2] South Cent Univ Nationalities, Hubei Key Lab Catalysis & Mat Sci, Wuhan, Peoples R China
[3] Chinese Acad Sci, Inst Chem, CAS Key Lab Colloid Interface & Chem Thermodynam, Beijing Natl Lab Mol Sci, Beijing, Peoples R China
[4] Wuhan Univ Sci & Technol, State Key Lab Refractories & Met, Wuhan, Peoples R China
基金
中国国家自然科学基金;
关键词
KETONES; CONVERSION; CATALYSTS; ESTERS; AIR; OXYGENATION; PERFORMANCE; ACTIVATION; EFFICIENT; ALDEHYDES;
D O I
10.1038/s41467-021-25118-0
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Selective cleavage of C-C bonds is very important in organic chemistry, but remains challenging because of their inert chemical nature. Herein, we report that Zn/NC-X catalysts, in which Zn2+ coordinate with N species on microporous N-doped carbon (NC) and X denotes the pyrolysis temperature, can effectively catalyze aerobic oxidative cleavage of C(CO)-C bonds and quantitatively convert acetophenone to methyl benzoate with a yield of 99% at 100 degrees C. The Zn/NC-950 can be applied for a wide scope of acetophenone derivatives as well as more challenging alkyl ketones. Detail mechanistic investigations reveal that the catalytic performance of Zn/NC-950 can be attributed to the coordination between Zn2+ and N species to change the electronic state of the metal, synergetic effect of the Zn single sites with their surrounding N atoms, as well as the microporous structure with the high surface area and structural defects of the NC. Selective cleavage of C-C bonds is very important in organic chemistry, but remains challenging because of their inert chemical nature. Here, the authors report that Zn2+ coordinated with N species on N-doped carbon catalysts can catalyze the aerobic oxidative cleavage and esterification of C(CO)-C bonds with high efficiency and activity.
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页数:12
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共 61 条
[1]   Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst [J].
Cao, Min ;
Yesilcimen, Ahmet ;
Wasa, Masayuki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (10) :4199-4203
[2]   Aerobic selective oxidation of methylaromatics to benzoic acids over Co@N/Co-CNTs with high loading CoN4 species [J].
Chen, Bingfeng ;
Li, Shaopeng ;
Liu, Shoujie ;
Dong, Minghua ;
Han, Buxing ;
Liu, Huizhen ;
Zheng, Lirong .
JOURNAL OF MATERIALS CHEMISTRY A, 2019, 7 (48) :27212-27216
[3]   Hierarchically Porous Co/CoxMy (M = P, N) as an Efficient Mott-Schottky Electrocatalyst for Oxygen Evolution in Rechargeable Zn-Air Batteries [J].
Chen, Jiangyue ;
Fan, Chuang ;
Hu, Xianyu ;
Wang, Chao ;
Huang, Zihan ;
Fu, Gengtao ;
Lee, Jong-Min ;
Tang, Yawen .
SMALL, 2019, 15 (28)
[4]   Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis [J].
Chen, Yilin ;
Du, Jianbo ;
Zuo, Zhiwei .
CHEM, 2020, 6 (01) :266-279
[5]   Performance of basic mixed oxides for aqueous-phase 5-hydroxymethylfurfural-acetone aldol condensation [J].
Cueto, Jennifer ;
Faba, Laura ;
Diaz, Eva ;
Ordonez, Salvador .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2017, 201 :221-231
[6]   Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance [J].
Das, Shoubhik ;
Addis, Daniele ;
Zhou, Shaolin ;
Junge, Kathrin ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1770-+
[7]   Catalytic Carbon-Carbon σ Bond Activation: An Intramolecular Carbo-Acylation Reaction with Acylquinolines [J].
Dreis, Ashley M. ;
Douglas, Christopher J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :412-+
[8]   Robust bifunctional oxygen electrocatalyst with a "rigid and flexible" structure for air-cathodes [J].
Fu, Gengtao ;
Jiang, Xian ;
Chen, Yifan ;
Xu, Lin ;
Sun, Dongmei ;
Lee, Jong-Min ;
Tang, Yawen .
NPG ASIA MATERIALS, 2018, 10 :618-629
[9]   Recent Advances in Carbon-Based Bifunctional Oxygen Electrocatalysts for Zn-Air Batteries [J].
Fu, Gengtao ;
Tang, Yawen ;
Lee, Jong-Min .
CHEMELECTROCHEM, 2018, 5 (11) :1424-1434
[10]   Boosting Bifunctional Oxygen Electrocatalysis with 3D Graphene Aerogel-Supported Ni/MnO Particles [J].
Fu, Gengtao ;
Yan, Xiaoxiao ;
Chen, Yifan ;
Xu, Lin ;
Sun, Dongmei ;
Lee, Jong-Min ;
Tang, Yawen .
ADVANCED MATERIALS, 2018, 30 (05)