We have been trying some test reactions using previously obtained protocols (one from the 1930s), and the preliminary H-1 results from the first protocol is very promising. Today I found the two papers below, which use TFA and a metal-ion salt of nitrate or nitrite. We are looking for references to other TFA-based methods, just in case our first methods fail.
https://pubs.rsc.org/en/content/articlepdf/1978/p1/p19780001076S Uemura et al., J Chem Soc Perkin I 1076-1079 1978.
https://jcsp.org.pk/ArticleUpload/1368-6161-1-RV.pdfMunawar and Khalid 2004
From the first reference: "A typical procedure is given. To a stirred solution of toluene (0.184 g, 2 mmol) in trifluoroacetic acid (15 ml) was added solid sodium nitrite (0.414g, 6 mmol) in one portion a t 25 "C. The resulted dark brown mixture was stirred for 8 h at 25 "C during which period the mixture turned orange, water (100 ml) was added, and the solution was extracted with benzene (3 x 50 ml)...Reactions with sodium nitrate were carried out similarly." The substrates in the second reference were haloaromatics, and the conditions were 90 °C. I don't think that their substrates are similar to ours, and I doubt that I would try this method as is.
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