Photoredox catalysis in the synthesis of γ- and δ-lactams from N-alkenyl trichloro- and dichloroacetamides

Abstract

The first blue light-mediated synthesis of γ- and δ-lactams from trichloroacetamides is reported in the presence of fac-Ir(ppy)3. Unlike previous works, these reactions are achieved under an air atmosphere with...

Catalyst-free photo-induced aerobic radical synthesis of lactams from N-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light

“…Moreover, when the reaction was monitored by 1 H NMR spectroscopy, we discovered that it had concluded within just 4 hours (entry 25). As it was commented in our previous work, 12 here also the reactions were carried out under non-anhydrous conditions in an aerobic environment showing a full tolerance to air and moisture.…”

“…aReactions were performed with 1a (0.2 mmol scale) in solvent (4 mL, 0.05 M) at rt and under air atmosphere, blue LEDs (435–445 nm), violet LEDs (395–405 nm).bSee ref. 12.cFor the results achieved from other substrates see the ESI.†dConversion 57%.eReaction achieved from 2 mmol of 1a in 40 mL of solvent.fTraces.gIn toluene, DCM, AcOEt, ethanol, acetone, DMSO, MeCN, water, dioxane or diisopropylether no reaction took place and 1a was recovered.hConversion 27%.…”

“…11 Recently we reported the first air-tolerant photocatalyzed synthesis of γand δ-lactams from trichloroacetamides under blue LEDs irradiation and non-anhydrous conditions. 12 In this investigation the best results were achieved in the presence of 1 mol% of Ir( ppy) 3 as the photocatalyst, N,N-diisopropylethylmine (5 equiv.) in a mixture of THF and acetone as a solvent.…”