Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

被引：11
作者：
Shen, Tong [1 ,2 ]
Liu, Shuai [2 ]
Zhao, Jianyou [1 ]
Wang, Nengyong [1 ]
Yang, Le [1 ]
Wu, Jintao [1 ]
Shen, Xu [1 ]
Liu, Zhong-Quan [1 ]
机构：
[1] Nanjing Univ Chinese Med, Coll Pharm, Jiangsu Collaborat Innovat Ctr Chinese Med Resour, Nanjing 210023, Peoples R China
[2] Univ Bordeaux, Inst Mol Sci, F-33405 Talence, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 05期
基金：
中国国家自然科学基金;
关键词：
ELECTRON-TRANSFER; CARBON; ACTIVATION; LIGHT; PALLADIUM; CHLORIDES; STRATEGY; ANILINES; ALKENES; CASCADE;
D O I：
10.1021/acs.joc.1c02947
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An electrochemistry-promoted oxidative cleavage of (sp(3))C-C(sp(3))/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.
引用
收藏
页码：3286 / 3295
页数：10
相关论文
共 82 条
[51]   Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides [J].
Semenok, Dmitrii ;
Kletskov, Alexey ;
Dikusar, Evgenij ;
Potkin, Vladimir ;
Lukin, Oleg .
TETRAHEDRON LETTERS, 2018, 59 (04) :372-374
[52]   Cu(II)-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level [J].
Sharma, Satyasheel ;
Park, Jihye ;
Kim, Mirim ;
Kwak, Jong Hwan ;
Jung, Young Hoon ;
Kim, In Su .
TETRAHEDRON, 2013, 69 (45) :9391-9397
[53]   Electrochemical Oxidation Induced Selective C-C Bond Cleavage [J].
Shi, Shi-Hui ;
Liang, Yujie ;
Jiao, Ning .
CHEMICAL REVIEWS, 2021, 121 (01) :485-505
[54]   ELECTROORGANIC CHEMISTRY .87. INDIRECT ELECTROOXIDATION OF AMINES TO NITRILES USING HALOGEN IONS AS MEDIATORS [J].
SHONO, T ;
MATSUMURA, Y ;
INOUE, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) :6075-6076
[55]   Ligand-modulated palladium-catalyzed aerobic alcohol oxidations [J].
Sigman, MS ;
Jensen, DR .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (03) :221-229
[56]   Hydrodealkenylative C(sp3)-C(sp2) bond fragmentation [J].
Smaligo, Andrew J. ;
Swain, Manisha ;
Quintana, Jason C. ;
Tan, Mikayla F. ;
Kim, Danielle A. ;
Kwon, Ohyun .
SCIENCE, 2019, 364 (6441) :681-+
[57]   Selective Carbon-Carbon Bond Cleavage of Cyclopropylamine Derivatives [J].
Sokolova, Olga O. ;
Bower, John F. .
CHEMICAL REVIEWS, 2021, 121 (01) :80-109
[58]   Catalytic activations of unstrained C-C bond involving organometallic intermediates [J].
Song, Feijie ;
Gou, Ting ;
Wang, Bi-Qin ;
Shi, Zhang-Jie .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (18) :7078-7115
[59]   Catalytic Aerobic Oxidation of C(sp3)-H Bonds [J].
Sterckx, Hans ;
Morel, Benedicte ;
Maes, Bert U. W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (24) :7946-7970
[60]   Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins [J].
Swain, Manisha ;
Sadykhov, Gusein ;
Wang, Ruoxi ;
Kwon, Ohyun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (40) :17565-17571
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