Science of Synthesis

Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 116.

Indoles can be obtained directly from arenes carrying an alkynyl substituent ortho to an amino or acylamino substituent; such starting materials are readily obtained by metal-catalyzed coupling of o-halo precursors. The coupling chemistry of aryl halides is covered per se elsewhere in Science of Synthesis, but must be mentioned here too since in some instances the coupling conditions lead on to cyclization in the same pot and thus the isolation of indoles as products. Indole syntheses in which the alkynylarene is converted first into an isolated intermediate in which the future indole α-carbon is an aldehyde/ketone (or equivalent), are covered in Sections ‌10.13.1.1.1.4.1.1.5‌ and ‌10.13.1.1.1.4.1.1.4‌. Indole syntheses in which the coupling of an aryl halide (carrying an ortho nitrogen substituent) and an alkyne, and the ring closure, take place in the same pot, without isolation of an intermediate, are covered in Section ‌10.13.1.1.1.3.1.9‌.

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