Regio- and chemoselective direct generation of functionalized aromatic aluminum compounds using aluminum ate base

Masanobu Uchiyama, Hiroshi Naka, Yotaro Matsumoto, Tomohiko Ohwada

Research output: Contribution to journalArticle

111 Citations (Scopus)

Abstract

A regio- and chemoselective direct method for generation of functionalized aromatic aluminum compounds through deprotonative directed ortho-alumination using triisobutyl(tetramethylpiperidino)aluminate ( iBu 3Al(TMP)Li), prepared by mixing of triisobutylaluminum ( iBu 3Al) and lithium tetramethylpiperidide (LTMP) in THF, has been developed. Deprotonative alumination of various functionalized benzenes with the use of iBu 3Al(TMP)Li proved effective for the direct generation of various ortho-functionalized aluminum aromatic and heteroaromatic derivatives, particularly those with electrophilic functional groups such as cyano, amide, and halogen. Direct alumination, followed by electrophilic trapping (with I 2), provided a convenient preparative method for 1,2- or 1,2,3-multisubstituted aromatic compounds. The functionalized aromatic aluminate intermediate also was found to undergo copper- and palladium-catalyzed C-C bond-forming reactions very efficiently and highly regio- and chemoselectively.

Original languageEnglish
Pages (from-to)10526-10527
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number34
DOIs
Publication statusPublished - 2004 Sep 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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