Photoinduced Synthesis of 2-Trifluoromethylated Indoles through Oxidative Trifluoromethylation Using Langlois’ Reagent in the Absence of External Photocatalyst

Samarpita Das; Harish K. Indurthi; Amita Kumari; Deepak K. Sharma

doi:10.1055/s-0040-1720093

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(24): 4096-4102
DOI: 10.1055/s-0040-1720093

paper

Photoinduced Synthesis of 2-Trifluoromethylated Indoles through Oxidative Trifluoromethylation Using Langlois’ Reagent in the Absence of External Photocatalyst

Authors

Samarpita Das

^aDepartment of Pharmaceutical Engineering and Technology, Indian Institute of Technology-Banaras Hindu University (IIT-BHU), Varanasi-221005, U.P., India
Harish K. Indurthi

^aDepartment of Pharmaceutical Engineering and Technology, Indian Institute of Technology-Banaras Hindu University (IIT-BHU), Varanasi-221005, U.P., India
Amita Kumari

^bCSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176061, India
Deepak K. Sharma ∗

^aDepartment of Pharmaceutical Engineering and Technology, Indian Institute of Technology-Banaras Hindu University (IIT-BHU), Varanasi-221005, U.P., India

Abstract

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Abstract

A photoinduced approach for regioselective C-2 trifluoromethylation of indoles was achieved with CF₃SO₂Na under UV light irradiation (360–365 nm) at ambient conditions without any external photo activator. The key steps involve the in situ conversion of CF₃SO₂Na reagent to CF₃ ^• radical under oxygen or air and UV irradiation. This proficient method has the advantages of mild reaction conditions, fair substrate tolerability, and gram scalability.

Key words

indole - Langlois reagent - trifluoromethylation - UV light irradiation - single electron transfer

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Referenzen

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