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
[21]   Expedient Synthesis of N-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C-H Bonds with Isocyanates [J].
Hesp, Kevin D. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (30) :11430-11433
[22]   Iron-Catalyzed Decarboxylative Alkyl Etherification of Vinylarenes with Aliphatic Acids as the Alkyl Source [J].
Jian, Wujun ;
Ge, Liang ;
Jiao, Yihang ;
Qian, Bo ;
Bao, Hongli .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) :3650-3654
[23]   Direct C-H Functionalization of Enamides and Enecarbamates by Using Visible-Light Photoredox Catalysis [J].
Jiang, Heng ;
Huang, Chengmei ;
Guo, Jiajia ;
Zeng, Chuanqi ;
Zhang, Yan ;
Yu, Shouyun .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) :15158-15166
[24]   Recent advances in reactions using diacyl peroxides as sources of O- and C-functional groups [J].
Kawamura, Shintaro ;
Mukherjee, Subrata ;
Sodeoka, Mikiko .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (10) :2096-2109
[25]   Perfluoroalkylation of Unactivated Alkenes with Acid Anhydrides as the Perfluoroalkyl Source [J].
Kawamura, Shintaro ;
Sodeoka, Mikiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) :8740-8743
[26]   Cu-mediated enamide formation in the total synthesis of complex peptide natural products [J].
Kuranaga, Takefumi ;
Sesoko, Yusuke ;
Inoue, Masayuki .
NATURAL PRODUCT REPORTS, 2014, 31 (04) :514-532
[27]   Copper-Catalyzed Cross-Coupling of Alkyl and Phosphorus Radicals for C(sp3)-P Bond Formation [J].
Li, Cheng-Kun ;
Tao, Ze-Kun ;
Shoberu, Adedamola ;
Zhang, Wei ;
Zou, Jian-Ping .
ORGANIC LETTERS, 2022, :6083-6087
[28]   Copper-Catalyzed Regioselective 1,2-Alkylesterification of Dienes to Allylic Esters [J].
Li, Yougui ;
Han, Yulong ;
Xiong, Haigen ;
Zhu, Nengbo ;
Qian, Bo ;
Ye, Changqing ;
Kantchev, Eric Assen B. ;
Bao, Hongli .
ORGANIC LETTERS, 2016, 18 (03) :392-395
[29]   Diacyl peroxides: practical reagents as aryl and alkyl radical sources [J].
Liu, Han ;
Yu, Jin-Tao ;
Pan, Changduo .
CHEMICAL COMMUNICATIONS, 2021, 57 (55) :6707-6724
[30]   Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds [J].
Liu, Wen ;
Pu, Maoping ;
He, Jun ;
Zhang, Tinghui ;
Dong, Shunxi ;
Liu, Xiaohua ;
Wu, Yun-Dong ;
Feng, Xiaoming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (30) :11856-11863