Facile synthesis of 6-iodo-2,2′-dipivaloyloxy-1,1′-binaphthyl, a key intermediate of high reactivity for selective palladium-catalyzed monofunctionalization of the 1,1′-binaphthalene core

Csaba Fehér, Béla Urbán, László Ürge, Ferenc Darvas, József Bakos, Rita Skoda-Földes

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A high-yielding procedure for selective monoiodination of 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) is reported. 6-Iodo-2,2′-dipivaloyloxy-1,1′-binaphthyl, obtained in three steps starting from BINOL in 88% overall yield, proved to be a highly efficient substrate in various palladium-catalyzed coupling (Stille, Heck, Sonogashira, and Suzuki coupling) and carbonylation reactions compared to the analogous 6-bromo derivative.

Original languageEnglish
Pages (from-to)3629-3632
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number28
DOIs
Publication statusPublished - Jul 14 2010

Keywords

  • 1,1′-Binaphthyl derivatives
  • Carbonylation
  • Coupling reactions
  • Iodination
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Facile synthesis of 6-iodo-2,2′-dipivaloyloxy-1,1′-binaphthyl, a key intermediate of high reactivity for selective palladium-catalyzed monofunctionalization of the 1,1′-binaphthalene core'. Together they form a unique fingerprint.

  • Cite this