KIO3-Catalyzed Aerobic Cross-Coupling Reactions of Enaminones and Thiophenols: Synthesis of Polyfunctionalized Alkenes by Metal-Free C-H Sulfenylation

被引:152
作者
Wan, Jie-Ping [1 ]
Zhong, Shanshan [1 ]
Xie, Lili [1 ]
Cao, Xiaoji [2 ]
Liu, Yunyun [1 ]
Wei, Li [1 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[2] Zhejiang Univ Technol, Res Ctr Anal & Measurement, 18 Chaowang Rd, Hangzhou 310014, Zhejiang, Peoples R China
关键词
CATALYZED OXIDATIVE CYCLIZATION; HECK-TYPE REACTION; N-ARYL ENAMINES; BOND FORMATION; ETHYL LACTATE; REGIOSELECTIVE SULFENYLATION; CYCLIC ENAMINONES; DIRECT ARYLATION; PALLADIUM; FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.5b03608
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of polyfunctionalized aminothioalkenes has been realized via the direct C-H sulfenylation of enaminones and analogous enamines. These cross-coupling reactions have been achieved by simple KIO3 catalysis under aerobic conditions without employing any transition metal catalyst or additional oxidant. The employment of bio-based green solvent ethyl lactate as the reaction medium constitutes another sustainable feature of the present work.
引用
收藏
页码:584 / 587
页数:4
相关论文
共 76 条
[1]   Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature [J].
Antonchick, Andrey P. ;
Samanta, Rajarshi ;
Kulikov, Katharina ;
Lategahn, Jonas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8605-8608
[2]   The green solvent ethyl lactate: an experimental and theoretical characterization [J].
Aparicio, Santiago ;
Alcalde, Rafael .
GREEN CHEMISTRY, 2009, 11 (01) :65-78
[3]   Metal-free sp3 C-H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes [J].
Badsara, Satpal Singh ;
Liu, Yi-Chen ;
Hsieh, Ping-An ;
Zeng, Jing-Wen ;
Lu, Shao-Yi ;
Liu, Yi-Wei ;
Lee, Chin-Fa .
CHEMICAL COMMUNICATIONS, 2014, 50 (77) :11374-11377
[4]   Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines [J].
Bennett, Jacqueline S. ;
Charles, Kaitlyn L. ;
Miner, Matthew R. ;
Heuberger, Caitlin F. ;
Spina, Elijah J. ;
Bartels, Michael F. ;
Foreman, Taylor .
GREEN CHEMISTRY, 2009, 11 (02) :166-168
[5]   Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol [J].
Bi, Lei ;
Georg, Gunda I. .
ORGANIC LETTERS, 2011, 13 (20) :5413-5415
[6]   Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides [J].
Bloome, Kayla S. ;
McMahen, Rebecca L. ;
Alexanian, Erik J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20146-20148
[7]   Visible-Light-Induced C=C Bond Cleavage of Enaminones for the Synthesis of 1,2-Diketones and Quinoxalines in Sustainable Medium [J].
Cao, Shuo ;
Zhong, Shanshan ;
Xin, Luoting ;
Wan, Jie-Ping ;
Wen, Chengping .
CHEMCATCHEM, 2015, 7 (09) :1478-1482
[8]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963
[9]   Bronsted Acid Mediated Cyclization of Enaminones. Rapid and Efficient Access to the Tetracyclic Framework of the Strychnos Alkaloids [J].
Edwankar, Rahul V. ;
Edwankar, Chitra R. ;
Namjoshi, Ojas A. ;
Deschamps, Jeffrey R. ;
Cook, James M. .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (02) :181-188
[10]   Melamine and Melamine-Formaldehyde Polymers as Ligands for Palladium and Application to Suzuki-Miyaura Cross-Coupling Reactions in Sustainable Solvents [J].
Edwards, Grant A. ;
Trafford, Mitchell A. ;
Hamilton, Alaina E. ;
Buxton, Audrey M. ;
Bardeaux, Matthew C. ;
Chalker, Justin M. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (05) :2094-2104