AgSCF3/Na2S2O8-Promoted Trifluoromethylthiolation/Cyclization of o-Propargyl Arylazides/ o-Alkynyl Benzylazides: Synthesis of SCF3-Substituted Quinolines and Isoquinolines

Yi-Feng Qiu; Yue-Jie Niu; Xi Wei; Bao-Qian Cao; Xi-Cun Wang; Zheng-Jun Quan

doi:10.1021/acs.joc.9b00181

AgSCF₃/Na₂S₂O₈-Promoted Trifluoromethylthiolation/Cyclization of o-Propargyl Arylazides/ o-Alkynyl Benzylazides: Synthesis of SCF₃-Substituted Quinolines and Isoquinolines

J Org Chem. 2019 Apr 5;84(7):4165-4178. doi: 10.1021/acs.joc.9b00181. Epub 2019 Mar 13.

Authors

Yi-Feng Qiu¹, Yue-Jie Niu¹, Xi Wei¹, Bao-Qian Cao¹, Xi-Cun Wang¹, Zheng-Jun Quan^{1

2}

Affiliations

¹ College of Chemistry and Chemical Engineering , Northwest Normal University , Lanzhou , Gansu 730070 , People's Republic of China.
² Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials , Lanzhou , Gansu 730070 , People's Republic of China.

PMID: 30835121
DOI: 10.1021/acs.joc.9b00181

Abstract

A AgSCF₃/Na₂S₂O₈-promoted trifluoromethylthiolation/cascade cyclization of o-propargyl arylazides (or o-alkynyl benzylazides) triggered by a carbon-carbon triple bond is reported. This strategy provides the synthesis of valuable SCF₃-substituted quinoline and isoquinoline systems via the construction of one C(sp²)-SCF₃ bond and one C-N bond within one process.