It has been awhile since I looked this approach….many, many years. I once thought the Julia indole formation reaction was unique, and as it turns out that it is the case. Comeon, I dare you to find a citation with a microwave approach to indoles using this method…..so I will work with that premise today. Back in the mid-80s (Tett Lett 1986), Sylvestre Julia converted a sulfinamide into an indole with heat in toluene (I know this might be dating me a bit). See…

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Aniline converted into sulfinamide rearrangment then ring closure Voila!

I see the delta so I know what I want to do. I got this from D. Taber’s Indole classification review in Tetrahedron 2011. I enjoyed the article but I bunched each of the “Type 1-9 ” classifications into heat — have to tell you there are a bunch. I jumbled the classifications and went looking for examples used in the literature — and this reaction didn’t have any follow-up to speak of….and I can’t figure out why. Anilines with SOCl2 the vinyl magnesium chloride then, for me, a microwave……zelch, nada. Anyway I am hopeful there is some utility to this reaction I am missing..maybe people aren’t that into making more indoles. Since this could be thought of as a [3,3] sigmatropic rearrangement, I think I can open up my search a bit and create a new category.

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