Photoelectrochemical Iron-Nickel Synergistic Catalysis for C(sp3)-H and Dehydroxymethylative Acylation

被引:0
作者
Zhou, Xiao [1 ]
Zhong, Ping-Fu [1 ]
Li, Zhuohua [1 ]
Hu, Pengwei [1 ]
Tu, Jialin [1 ]
Yang, Chao [1 ]
Guo, Lin [1 ]
Xia, Wujiong [1 ,3 ]
Chen, Tingting [2 ]
机构
[1] Harbin Inst Technol Shenzhen, Sch Sci, State Key Lab Urban Water Resource & Environm, Shenzhen 518055, Peoples R China
[2] Dinghe Property Insurance Co, Shenzhen 518055, Peoples R China
[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
H BOND FUNCTIONALIZATION; ORGANOMETALLIC REAGENTS; CHLORIDES;
D O I
10.1021/acs.orglett.5c01884
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed an iron-nickel dual-catalytic system for efficient C(sp3)-H activation acylation of hydrocarbons and carboxylic acids under photoelectrochemical conditions. This system is based on ligand-to-metal charge transfer-mediated direct hydrogen atom transfer and is applicable to inert C(sp3)-H-containing compounds. It also enables dehydroxymethylative acylation of alcohols, both these two reactions demonstrating broad substrate scope and unconventional chemoselectivity. Gram-scale synthesis, flow chemistry, and mechanistic studies highlight its potential in sustainable C(acyl)-C bond formation.
引用
收藏
页码:6995 / 7000
页数:6
相关论文
共 37 条
[21]   Decatungstate Catalyzed Photochemical Acetylation of C(sp3)-H Bonds [J].
Liu, Qinglong ;
Ding, Yuzhen ;
Gao, Yuxi ;
Yang, Yunhong ;
Gao, Lijun ;
Pan, Zhiqiang ;
Xia, Chengfeng .
ORGANIC LETTERS, 2022, :7983-7987
[22]   Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis [J].
Malapit, Christian A. ;
Prater, Matthew B. ;
Cabrera-Pardo, Jaime R. ;
Li, Min ;
Pham, Tammy D. ;
McFadden, Timothy Patrick ;
Blank, Skylar ;
Minteer, Shelley D. .
CHEMICAL REVIEWS, 2022, 122 (03) :3180-3218
[23]   Experimental and Calculated Electrochemical Potentials of Common Organic Molecules for Applications to Single-Electron Redox Chemistry [J].
Roth, Hudson G. ;
Romero, Nathan A. ;
Nicewicz, David A. .
SYNLETT, 2016, 27 (05) :714-723
[24]   Site- and enantioselective cross-coupling of saturated N-heterocycles with carboxylic acids by cooperative Ni/photoredox catalysis [J].
Shu, Xiaomin ;
Zhong, De ;
Huang, Qian ;
Huan, Leitao ;
Huo, Haohua .
NATURE COMMUNICATIONS, 2023, 14 (01)
[25]   Photoinduced Site-Selective Functionalization of Aliphatic C-H Bonds by Pyridine N-oxide Based HAT Catalysts [J].
Wang, Ban ;
Pettenuzzo, Cristina Ascenzi ;
Singh, Jujhar ;
Mccabe, Gavin E. ;
Clark, Logan ;
Young, Ryan ;
Pu, Jingzhi ;
Deng, Yongming .
ACS CATALYSIS, 2022, 12 (16) :10441-10448
[26]   Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids [J].
Wang, Jiang ;
Hoerrner, Megan E. ;
Watson, Mary P. ;
Weix, Daniel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (32) :13484-13489
[27]   Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters [J].
Wang, Jiang ;
Cary, Brian P. ;
Beyer, Peyton D. ;
Gellman, Samuel H. ;
Weix, Daniel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) :12081-12085
[28]   Photoelectrochemical nickel-catalyzed carboacylation/silanoylation of alkenes with unactivated C/Si-H bonds [J].
Wang, Lanfen ;
Huo, Xiangyu ;
He, Xiaozhi ;
Ackermann, Lutz ;
Wang, Dingyi .
GREEN CHEMISTRY, 2024, 26 (14) :8315-8322
[29]   Synthesis of C-acyl furanosides via the cross-coupling of glycosyl esters with carboxylic acids [J].
Wei, Yongliang ;
Lam, Jenny ;
Diao, Tianning .
CHEMICAL SCIENCE, 2021, 12 (34) :11414-11419
[30]   Palladium-catalyzed carbonylative coupling reactions between Ar-X and carbon nucleophiles [J].
Wu, Xiao-Feng ;
Neumann, Helfried ;
Beller, Matthias .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4986-5009