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DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (2010254.

In one of the most direct indole syntheses to have been devised, 1,2-diols 198, even ethane-1,2-diol itself, react at 180°C with arylamines 197 under the influence of dichlorotris(triphenylphosphine)ruthenium(II) to give indoles 199 (Scheme 64); hydrogen gas is evolved.[‌217‌] Triethanolamine also serves to provide a two-carbon fragment in reactions with N-alkylarylamines using the same catalyst,[‌218‌] and in the presence of tin(II) chloride N-unsubstituted indoles, e.g. 200, can be formed from primary arylamines.[‌219‌] More substituted triethanolamines, e.g. tris(2-hydroxypropyl)amine {[HOCH(Me)CH2]3N} as its hydrochloride salt, react in the same way, using ruthenium(III) chloride hydrate, triphenylphosphine, and tin(II) chloride dihydrate in aqueous 1,4-dioxane at 180°C, giving 2-methyl-1H-indole in this particular example.[‌220‌]

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8-Meeeee-8M-eeeeee (888, M8 = Me; M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

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8,8-Meeeeeee-8M-eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

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