One-step synthesis of α-fluoroarylacetic acids from trifluoromethyl arenes via photocatalytic reduction
5 affiliations
- 1Department of Chemistry, Graduate School of Science, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe, Japan, 657-8501
- 2Graduate School of Informatics
- 3Nagoya University
- 4Department of Chemistry, School of Science
- 5China Pharmaceutical University
Abstract
A photocatalytic reduction strategy for the direct synthesis of α-fluoroarylacetic acids from readily available trifluoromethyl arenes has been developed. In contrast to conventional approaches, this reaction does not generate undesired oxidation byproducts associated with the use of fluorinating reagents. Investigation of the substrate scope revealed that the reaction tolerates a wide range of functional groups, including dimethylamino, alkynyl, alkenyl, and ether functionalities. Trifluoromethyl-substituted pyridine derivatives were also compatible with the reaction conditions. Mechanistic studies suggested that the reaction proceeds via an initial hydrodefluorination to form a difluoromethyl arene intermediate, followed by further reductive C–F bond cleavage and carboxylation. The observed selectivity for the monofluorinated products originated from the selective carboxylation during product formation together with the slow hydrodefluorination of the resulting α-fluoroarylacetic acids. The reaction proceeds without the need for an external CO2 atmosphere.
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BibTeX
@misc{kuang2026onestep,
title = {{One-step synthesis of α-fluoroarylacetic acids from trifluoromethyl arenes via photocatalytic reduction}},
author = {Huilong Kuang and Suguru Murakami and Tatsushi Yabuta and Masahiro Higashi and Weibin Xie and Ryosuke Matsubara},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010504/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010504/v1},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - One-step synthesis of α-fluoroarylacetic acids from trifluoromethyl arenes via photocatalytic reduction
AU - Huilong Kuang
AU - Suguru Murakami
AU - Tatsushi Yabuta
AU - Masahiro Higashi
AU - Weibin Xie
AU - Ryosuke Matsubara
PY - 2026
DA - 2026/10/15
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010504/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010504/v1
AB - A photocatalytic reduction strategy for the direct synthesis of α-fluoroarylacetic acids from readily available trifluoromethyl arenes has been developed. In contrast to conventional approaches, this reaction does not generate undesired oxidation byproducts associated with the use of fluorinating reagents. Investigation of the substrate scope revealed that the reaction tolerates a wide range of functional groups, including dimethylamino, alkynyl, alkenyl, and ether functionalities. Trifluoromethyl-substituted pyridine derivatives were also compatible with the reaction conditions. Mechanistic studies suggested that the reaction proceeds via an initial hydrodefluorination to form a difluoromethyl arene intermediate, followed by further reductive C–F bond cleavage and carboxylation. The observed selectivity for the monofluorinated products originated from the selective carboxylation during product formation together with the slow hydrodefluorination of the resulting α-fluoroarylacetic acids. The reaction proceeds without the need for an external CO2 atmosphere.
ER -