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Chromium-catalyzed migratory arylmagnesiation of unactivated alkynes

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Abstract

We report here on a chromium-catalyzed addition reaction of an arylmagnesium bromide to an unactivated internal alkyne to afford an ortho-alkenylarylmagnesium bromide. This reaction likely proceeds via the insertion of an alkyne into an arylchromium species, alkenyl-to-aryl 1,4-chromium migration, and transmetalation between the resulting arylchromium species and the starting aryl Grignard reagent. The product of this reaction is amenable to a series of electrophilic trapping reactions.

Graphical abstract: Chromium-catalyzed migratory arylmagnesiation of unactivated alkynes

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Publication details

The article was received on 31 May 2017, accepted on 28 Jun 2017 and first published on 29 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00427C
Citation: Org. Chem. Front., 2017, Advance Article
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    Chromium-catalyzed migratory arylmagnesiation of unactivated alkynes

    J. Yan and N. Yoshikai, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00427C

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