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10.13.1.1.1.2.1.3 Method 3: From o-Alkenylnitroarenes and o-Alkenylaryl Azides

DOI: 10.1055/sos-SD-010-00559

Joule, J. A.Science of Synthesis, (200110432.

Indoles can be obtained directly from arenes carrying a vinyl substituent ortho to a nitrogen substituent. This type of intermediate can in turn be readily obtained by metal-catalyzed coupling of o-halo precursors. In addition to metal-catalyzed couplings, there are four common methods used for the synthesis of o-nitrostyrenes: (1) reaction of an o-(bromomethyl)nitroarene with a phosphine then Wittig condensation with an aldehyde;[‌289‌] (2) Wittig reaction employing an o-nitroaraldehyde as the carbonyl component as in 390 391; (3) base-catalyzed condensation of a methyl group ortho to an aromatic nitro group with an aldehyde; and (4) ortho nitration of a styrene. Indole syntheses in which the vinyl group is functionalized at the future indole α-carbon, that is, in which the future indole α-carbon is at the oxidation level of aldehyde or ketone, are discussed in Sections 10.13.1.1.1.2.1.1.2 and 10.13.1.1.1.2.1.1.4.

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