A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

Aiichiro Nagaki, Heejin Kim, Yuya Moriwaki, Chika Matsuo, Jun Ichi Yoshida

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para-, meta-, and ortho-positions. Alkyl p- and m-lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o-lithiobenzoates were successfully generated by the Br/ Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.

Original languageEnglish
Pages (from-to)11167-11177
Number of pages11
JournalChemistry - A European Journal
Volume16
Issue number36
DOIs
Publication statusPublished - 2010 Sep 24
Externally publishedYes

Keywords

  • Aryllithium
  • Flash chemistry
  • Microreactors
  • Organometallic compounds
  • Protecting groups

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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