Photocatalytic chemo-, regio- & stereoselective olefinic β-C-H decarboxylative alkylation of enamides with diacyl peroxides

被引:12
作者
Liu, Han [1 ]
Wu, Yechun [1 ]
Liu, Lingli [1 ]
Yu, Jin-Tao [1 ]
Pan, Changduo [1 ,2 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Changzhou 213164, Peoples R China
[2] Jiangsu Univ Technol, Sch Chem & Chem Engn, Changzhou 213001, Peoples R China
基金
中国国家自然科学基金;
关键词
C(SP(2))-H ARYLSULFONYLATION; UNACTIVATED ALKENES; ACID ANHYDRIDES; SULFUR-DIOXIDE; FUNCTIONALIZATION; VINYLARENES; BONDS; ALKYNYLATION; OLEFINATION; ACYLATION;
D O I
10.1039/d3cc01908j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A decarboxylative alkylation of enamides with alkyl diacyl peroxides induced by visible-light is described. The chemo-, regio- and stereoselective olefinic beta-C-H alkylation generates a series of primary- and secondary alkylated enamides in yields up to 95%. This transformation bears the advantages of operational simplicity, good functional group compatibility and mild conditions.
引用
收藏
页码:8556 / 8559
页数:4
相关论文
共 71 条
[1]   Iron-Catalyzed C-H Alkylation of Heterocyclic C-H Bonds [J].
Babu, Kaki Raveendra ;
Zhu, Nengbo ;
Bao, Hongli .
ORGANIC LETTERS, 2017, 19 (01) :46-49
[2]   Iron catalyzed β-C(sp2)-H alkylation of enamides [J].
Bertho, Sylvain ;
Maazaoui, Radhouan ;
Torun, Damla ;
Dondasse, Ismael ;
Abderrahim, Raoudha ;
Nicolas, Cyril ;
Gillaizeau, Isabelle .
NEW JOURNAL OF CHEMISTRY, 2021, 45 (37) :17475-17482
[3]   β-C(sp2)-H alkylation of enamides using xanthate chemistry [J].
Bertho, Sylvain ;
Dondasse, Ismael ;
Retailleau, Pascal ;
Nicolas, Cyril ;
Gillaizeau, Isabelle .
NEW JOURNAL OF CHEMISTRY, 2020, 44 (17) :7129-7141
[4]   RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].
Besset, Tatiana ;
Kuhl, Nadine ;
Patureau, Frederic W. ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171
[5]  
Cai Z., 2018, J ORG CHEM, V83, P5149
[6]   Enamides: valuable organic substrates [J].
Carbery, David R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460
[7]   Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides [J].
Chang, Xi-Hao ;
Wang, Zi-Lu ;
Zhao, Meng ;
Yang, Chao ;
Li, Jie-Jun ;
Ma, Wei-Wei ;
Xu, Yun-He .
ORGANIC LETTERS, 2020, 22 (04) :1326-1330
[8]   Palladium-Catalyzed Oxidative Carbonylation of the Alkenyl C-H Bonds of Enamides: Synthesis of 1,3-Oxazin-6-ones [J].
Chen, Ming ;
Ren, Zhi-Hui ;
Wang, Yao-Yu ;
Guan, Zheng-Hui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14196-14199
[9]   Enamide Derivatives: Versatile Building Blocks for Total Synthesis [J].
Courant, Thibaut ;
Dagousset, Guillaume ;
Masson, Geraldine .
SYNTHESIS-STUTTGART, 2015, 47 (13) :1799-1826
[10]   Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in Three-Component Alkyl-Fluorination of Olefins with a Fluoride Ion [J].
Deng, Weili ;
Feng, Weiwei ;
Li, Yajun ;
Bao, Hongli .
ORGANIC LETTERS, 2018, 20 (14) :4245-4249