A comparative study of base-free arylcopper reagents for the transfer of aryl groups to boron halides

Anand Sundararaman, Frieder Jäkle

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62 Scopus citations

Abstract

A comparative study on the reactivity and selectivity of arylcopper species in reactions with boron halides was performed. Mesitylcopper reacts with BX3 (X=Cl, Br) in toluene at low temperature under highly selective formation of the monosubstituted boranes MesBX2. The dimesitylboranes Mes2BX are gradually formed with a twofold excess of the organocopper reagent at elevated temperature. In contrast, pentafluorophenylcopper shows a tendency for formation of B(C6F5) 3 in reactions with BX3 irrespective of the stoichiometry used, suggesting a strong impact of electronic factors on the selectivity of the aryl transfer reaction. New procedures for the synthesis of the pentafluorophenylboron halides C6 F5BX2 (X=Cl: 57%; X=Br: 62%) and of tris(pentafluorophenyl)borane (80%) and related mixed-substituted triarylboranes from the base-free isolable pentafluorophenylcopper precursor have been developed.

Original languageEnglish (US)
Pages (from-to)134-142
Number of pages9
JournalJournal of Organometallic Chemistry
Volume681
Issue number1-2
DOIs
StatePublished - Sep 12 2003

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Keywords

  • Arylation
  • Boron
  • Copper
  • Lewis acid
  • Organoborane
  • Organocopper reagent

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