Visible-light-induced Trifluoromethylation of highly functionalized arenes and heteroarenes in continuous flow

I. Abdiaj; C. Bottecchia; J. Alcazar; T. Noël

doi:10.1055/s-0036-1588527

Visible-light-induced Trifluoromethylation of highly functionalized arenes and heteroarenes in continuous flow

I. Abdiaj
, C. Bottecchia
, J. Alcazar
, T. Noël

Micro Flow Chemistry and Synthetic Methodology

Research output: Contribution to journal › Article › Academic › peer-review

59 Citations (Scopus)

319 Downloads (Pure)

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 (CF ₃ SO ₂ Na) as the trifluoromethylating agent and the iridium complex [Ir{dF(CF ₃)ppy} ₂ ](dtbpy)]PF ₆ 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.

Original language	English
Pages (from-to)	4978-4985
Number of pages	8
Journal	Synthesis
Volume	49
Issue number	22
DOIs	https://doi.org/10.1055/s-0036-1588527
Publication status	Published - 16 Nov 2017

Keywords

continuous flow
Langlois reagent
photoredox catalysis
trifluoromethylation
visible light

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10.1055/s-0036-1588527

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title = "Visible-light-induced Trifluoromethylation of highly functionalized arenes and heteroarenes in continuous flow",

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 (CF 3 SO 2 Na) as the trifluoromethylating agent and the iridium complex [Ir\{dF(CF 3)ppy\} 2 ](dtbpy)]PF 6 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.",

keywords = "continuous flow, Langlois reagent, photoredox catalysis, trifluoromethylation, visible light",

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T1 - Visible-light-induced Trifluoromethylation of highly functionalized arenes and heteroarenes in continuous flow

AU - Abdiaj, I.

AU - Bottecchia, C.

AU - Alcazar, J.

AU - Noël, T.

PY - 2017/11/16

Y1 - 2017/11/16

N2 - 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 (CF 3 SO 2 Na) as the trifluoromethylating agent and the iridium complex [Ir{dF(CF 3)ppy} 2 ](dtbpy)]PF 6 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.

AB - 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 (CF 3 SO 2 Na) as the trifluoromethylating agent and the iridium complex [Ir{dF(CF 3)ppy} 2 ](dtbpy)]PF 6 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.

KW - continuous flow

KW - Langlois reagent

KW - photoredox catalysis

KW - trifluoromethylation

KW - visible light

UR - https://www.scopus.com/pages/publications/85027110996

U2 - 10.1055/s-0036-1588527

DO - 10.1055/s-0036-1588527

M3 - Article

AN - SCOPUS:85027110996

SN - 0039-7881

VL - 49

SP - 4978

EP - 4985

JO - Synthesis

JF - Synthesis

IS - 22

ER -

Visible-light-induced Trifluoromethylation of highly functionalized arenes and heteroarenes in continuous flow

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Keywords

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