Synthesis of 2-Aryl Acetophenones via Hydrobromination and Oxy-isomerization of (o-Arylethynyl)benzyl Alcohols

Tzu Hsuan Kuan, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

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Abstract

Hydrobromination and oxy-isomerization of (o-arylethynyl)benzyl alcohols to yield brominated aryl ketones were achieved with bromotrimethylsilane. The substrate scope suggested that vinyl carbocations, stabilized by the conjugated aryl groups, are the reaction intermediates. 1H-Isochromene was also detected by 1H NMR, and an isolated 1H-isochromene was converted to the product when retreated with TMSBr. The formation of 1H-isochromene is equivalent to a 6-endo-dig cyclization and contrasts with the corresponding reactions under basic conditions, in which the 5-exo-dig process dominated.

Original languageEnglish
Pages (from-to)6907-6917
Number of pages11
JournalJournal of Organic Chemistry
Volume86
Issue number9
DOIs
StatePublished - 7 May 2021

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