TFA-Mediated DMSO-Participant
Sequential Oxidation/1,3-Dipolar
Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines

Shu, Wen-Ming; He, Jian-Xin; Zhang, Xun-Fang; Wang, Shuai; Wu, An-Xin

doi:10.1021/acs.joc.8b02755.s001

jo8b02755_si_001.pdf (3.43 MB)

TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines

journal contribution

posted on 2019-02-12, 15:12 authored by Wen-Ming Shu, Jian-Xin He, Xun-Fang Zhang, Shuai Wang, An-Xin Wu

A trifluoroacetic acid (TFA)-mediated cascade oxidation/1,3-dipolar cycloaddition reaction of stabilized pyridinium salts with dimethyl sulfoxide (DMSO) has been developed in the presence of K₂S₂O₈ and trimethylethylenediamine (TMEDA). In this transition-metal-free reaction, DMSO acts as a one-carbon source, thus providing a convenient method for the efficient and direct synthesis of various indolizine derivatives.