Trifluoromethylation of Arenes and Heterocycles via a Bench-Stable Photocaged Trifluoromethylation Reagent

Gavin J. Rustin; Vishal Agarwal; Penelope I. Dalton; Zenghui Jiang; Zhao Liu; Isabella G. Najor; Bahar Heydari; Beeta Heydari; Nicholas J. Kuehl; Vlad Kumirov; Michael T. Taylor; Jeffrey L. Gustafson

doi:10.1021/acs.orglett.5c04296

Trifluoromethylation of Arenes and Heterocycles via a Bench-Stable Photocaged Trifluoromethylation Reagent

Gavin J. Rustin
, Vishal Agarwal
, Penelope I. Dalton
, Zenghui Jiang
, Zhao Liu
, Isabella G. Najor
, Bahar Heydari
, Beeta Heydari
, Nicholas J. Kuehl
, Vlad Kumirov
, Michael T. Taylor
, Jeffrey L. Gustafson

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

Abstract

Herein we report a simple radical aromatic trifluoromethylation process that utilizes a cationic aromatic sulfonate ester as a trifluoromethyl radical photocage. This chemistry allows for the rapid and straightforward trifluoromethylation of diverse aromatics and heterocycles, including complex pharmaceuticals and natural products, with only the substrate, photocage, solvent, and 456 nm light in minutes.

Original language	English (US)
Pages (from-to)	13504-13508
Number of pages	5
Journal	Organic Letters
Volume	27
Issue number	49
DOIs	https://doi.org/10.1021/acs.orglett.5c04296
State	Published - Dec 12 2025
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c04296

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title = "Trifluoromethylation of Arenes and Heterocycles via a Bench-Stable Photocaged Trifluoromethylation Reagent",

abstract = "Herein we report a simple radical aromatic trifluoromethylation process that utilizes a cationic aromatic sulfonate ester as a trifluoromethyl radical photocage. This chemistry allows for the rapid and straightforward trifluoromethylation of diverse aromatics and heterocycles, including complex pharmaceuticals and natural products, with only the substrate, photocage, solvent, and 456 nm light in minutes.",

author = "Rustin, \{Gavin J.\} and Vishal Agarwal and Dalton, \{Penelope I.\} and Zenghui Jiang and Zhao Liu and Najor, \{Isabella G.\} and Bahar Heydari and Beeta Heydari and Kuehl, \{Nicholas J.\} and Vlad Kumirov and Taylor, \{Michael T.\} and Gustafson, \{Jeffrey L.\}",

year = "2025",

month = dec,

day = "12",

doi = "10.1021/acs.orglett.5c04296",

language = "English (US)",

volume = "27",

pages = "13504--13508",

journal = "Organic Letters",

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number = "49",

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TY - JOUR

T1 - Trifluoromethylation of Arenes and Heterocycles via a Bench-Stable Photocaged Trifluoromethylation Reagent

AU - Rustin, Gavin J.

AU - Agarwal, Vishal

AU - Dalton, Penelope I.

AU - Jiang, Zenghui

AU - Liu, Zhao

AU - Najor, Isabella G.

AU - Heydari, Bahar

AU - Heydari, Beeta

AU - Kuehl, Nicholas J.

AU - Kumirov, Vlad

AU - Taylor, Michael T.

AU - Gustafson, Jeffrey L.

PY - 2025/12/12

Y1 - 2025/12/12

N2 - Herein we report a simple radical aromatic trifluoromethylation process that utilizes a cationic aromatic sulfonate ester as a trifluoromethyl radical photocage. This chemistry allows for the rapid and straightforward trifluoromethylation of diverse aromatics and heterocycles, including complex pharmaceuticals and natural products, with only the substrate, photocage, solvent, and 456 nm light in minutes.

AB - Herein we report a simple radical aromatic trifluoromethylation process that utilizes a cationic aromatic sulfonate ester as a trifluoromethyl radical photocage. This chemistry allows for the rapid and straightforward trifluoromethylation of diverse aromatics and heterocycles, including complex pharmaceuticals and natural products, with only the substrate, photocage, solvent, and 456 nm light in minutes.

UR - https://www.scopus.com/pages/publications/105024810412

UR - https://www.scopus.com/pages/publications/105024810412#tab=citedBy

U2 - 10.1021/acs.orglett.5c04296

DO - 10.1021/acs.orglett.5c04296

M3 - Article

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AN - SCOPUS:105024810412

SN - 1523-7060

VL - 27

SP - 13504

EP - 13508

JO - Organic Letters

JF - Organic Letters

IS - 49

ER -

Trifluoromethylation of Arenes and Heterocycles via a Bench-Stable Photocaged Trifluoromethylation Reagent

Abstract

ASJC Scopus subject areas

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