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Intramolecular Vinylation of Aryl Rings by Vinyl Cations.

ABSTRACT: A Lewis acid mediated intramolecular electrophilic vinylation of aryl rings by vinyl cations is reported. This reaction takes advantage of ?-hydroxy-?-diazo ketones as vinyl cation precursors and provides good yields of tricyclic 1-indenones that contain a seven-membered ring. Extending the alkane chain that tethers the vinyl cation to the aromatic ring leads to 2-napthol and 2-indenone products.

SUBMITTER: Fang J

PROVIDER: S-EPMC7045802 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Intramolecular Vinylation of Aryl Rings by Vinyl Cations.

Fang Jian J Brewer Matthias M

Organic letters 20181114 23

A Lewis acid mediated intramolecular electrophilic vinylation of aryl rings by vinyl cations is reported. This reaction takes advantage of β-hydroxy-α-diazo ketones as vinyl cation precursors and provides good yields of tricyclic 1-indenones that contain a seven-membered ring. Extending the alkane chain that tethers the vinyl cation to the aromatic ring leads to 2-napthol and 2-indenone products. ...[more]

PMID: 30426753

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