Practical regioselective halogenation of vinylogous esters: Synthesis of differentiated mono-haloresorcinols and polyhalogenated resorcinols

Xiaohong Chen, Xiaoguang Liu, Jenny S. Martinez, Justin T. Mohr

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A practical and efficient method for the direct, regioselective conversion of vinylogous esters to haloresorcinols is reported. Control of the reaction conditions enables synthesis of either the 4- or 6-haloresorcinol isomers from a common precursor with excellent regiocontrol and high yield. The generality and functional group tolerance of this novel protocol is demonstrated. The utility of this methodology to access polyhaloresorcinols is also reported. These methods create useful functionalized building blocks for further synthetic applications.

Original languageEnglish (US)
Pages (from-to)3653-3665
Number of pages13
JournalTetrahedron
Volume72
Issue number26
DOIs
StatePublished - Jun 30 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Dienolates
  • Halogenation
  • Regioselectivity
  • Resorcinols
  • Sulfonyl halides

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