Organic Chemistry Portal

Abstracts

Search:

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: xyluoecust.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 (free Supporting Information)


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