Synthesis
DOI: 10.1055/s-0036-1588527
paper
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Induced Trifluoromethylation of Highly Functionalized Arenes and Heteroarenes in Continuous Flow

Irini Abdiaja, Cecilia Bottecchiab, Jesus Alcazar*a, Timothy Noёl*b
  • aJanssen Research & Development, Jarama 75A, 45007 Toledo, Spain   Email: jalcazar@its.jnj.com
  • bDepartment of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands   Email: t.noel@tue.nl
The authors acknowledge the European Union for a Marie Curie ITN Grant (Photo4Future, Grant No. 641861). Further financial support for this work was provided by a VIDI grant (T.N., SensPhotoFlow, No. 14150).
Further Information

Publication History

Received: 07 June 2017

Accepted after revision: 07 July 2017

Publication Date:
09 August 2017 (eFirst)

Abstract

We report a continuous-flow protocol for the trifluoromethylation of arenes, heteroarenes, and benzofused heterocycles. This photoredox methodology relies on the use of solid sodium trifluoromethanesulfinate (CF3SO2Na) as the trifluoromethylating agent and the iridium complex [Ir{dF(CF3)ppy}2](dtbpy)]PF6 as the photoredox catalyst. A diverse set of highly functionalized heterocycles proved compatible with the methodology, and moderate to good yields were obtained within 30 minutes of residence time.

Supporting Information