Photoredox Trifluoromethylation/Cyclization of N-Arylacrylamides with 4-(Difluoroamino)-1-[(trifluoromethyl)sulfonyl]pyridinium Triflate (TFSP)

Abstract

A photoredox trifluoromethylation/cyclization of N-arylacrylamides with inexpensive stable solid 4-(difluoroamino)-1-[(trifluoromethyl)sulfonyl]pyridinium triflate (TFSP) has been developed.

Key words

trifluoromethylation - cyclization - arylacrylamides - photo­redox reaction - indolones

Publication History

Received: 29 August 2022

Accepted after revision: 24 October 2022

Accepted Manuscript online:
24 October 2022

Article published online:
10 January 2023

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• 17 1,3-Dimethyl-3-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-indol-2-one (3a); Typical Procedure A dried reaction tube was charged with TFSP (0.25 mmol), 1a (0.20 mmol), PC4 (1 mol%), and Cs₂CO₃ (0.2 mmol). The tube was evacuated and backfilled with argon three times and then anhyd DCM (2.0 mL) was injected into the tube from a syringe. The solution was irradiated with 50 W 440 nm blue LEDs for 12 h. The crude mixture was purified by column chromatography (silica gel) to give a yellow oil; yield: 32.9 mg (68%). ¹H NMR (500 MHz, CDCl₃): δ = 7.33 (td, J = 7.7, 1.2 Hz, 1 H), 7.28 (d, J = 7.5 Hz, 1 H), 7.11 (td, J = 7.5, 1.0 Hz, 1 H), 6.90 (d, J = 7.8 Hz, 1 H), 3.25 (s, 3 H), 2.84 (dq, J = 15.2, 10.7 Hz, 1 H), 2.66 (dq, J = 15.2, 10.5 Hz, 1 H), 1.42 (s, 3 H).