Synthesis of Polysubstituted 3-Aminothiophenes from Thioamides and Allenes via Tandem Thio-Michael Addition/Oxidative Annulation and 1,2-Sulfur Migration
Teng Han, Yu Wang, Hong-Liang Li, Xiaoyan Luo* and Wei-Ping Deng*
*School of Pharmacy and Shanghai Key Laboratory of New Drug
Design, East China University of Science and Technology, 130 Meilong Road,
Shanghai 200237, China, Email: xyluo
ecust.edu.cn,
weiping_dengecust.edu.cn
T. Han, Y. Wang, H.-L. Li, X. Luo, W.-P. Deng, J. Org. Chem., 2018, 83, 1538-1542.
DOI: 10.1021/acs.joc.7b02616
Abstract
A TBAI/TBHP catalyst system enables a facile synthetis of highly functionalized 3-aminothiophenes from readily available allenes and thioamides in very good yields under mild reaction conditions via a tandem thio-Michael addition, oxidative annulation, and 1,2-sulfur migration pathway.
see article for more examples
proposed mechanism
Key Words
Thiophenes, tert-Butyl hydroperoxide
ID: J42-Y2018
