A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

Jaeyoung Ko, Jungyeob Ham, Inho Yang, Jungwook Chin, Sang Jip Nam, Heonjoong Kang

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16 Scopus citations

Abstract

A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ protection of the hydroxy or carboxylic acid group by reaction with a Grignard reagent, lithium-halogen exchange, the formation of lithium thiolates, and the nucleophilic attack of lithium thiolates on various electrophiles without isolation of the thiolates, in one vessel. This procedure required a very short reaction time (1-1.5 h) and gave the corresponding sulfides in 75-97% yields.

Original languageEnglish
Pages (from-to)7101-7106
Number of pages6
JournalTetrahedron Letters
Volume47
Issue number39
DOIs
StatePublished - 25 Sep 2006

Keywords

  • Grignard reagent
  • Halogen lithium exchange
  • Hydroxylated and carboxylated aryl alkyl sulfides
  • Lithium aryl thiolates
  • Sulfur
  • Thioethers

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