Organocatalytic vinyl and Friedel-Crafts alkylations with trifluoroborate salts

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Abstract

Herein we report the first use of vinyl and heteroaryl trifluoroborate salts as viable substrates for amine-catalyzed conjugate additions. The application of LUMO-lowering iminium catalysis has enabled the highly regio- and enantioselective 1,4-addition of rationally designed trifluoroborate salt nucleophiles to α,β-unsaturated aldehydes. Imidazolidinone 2•HCl was found to catalyze the addition of various BF3K-derived heteroaryl and vinyl species to a range of enals with excellent levels of enantioselectivity. Importantly, the use of these salts can enable nontraditional regiocontrol as part of a Friedel-Crafts pathway. Boronic acids can also be employed as viable π-nucleophiles for these asymmetric conjugate additions provided that in situ activation to the corresponding boronate species is accomplished. While BF3K salts are routinely employed in transition metal catalysis, to our knowledge, this is the first use of this activation group for organic catalysis or Friedel-Crafts alkylations.

Original languageEnglish (US)
Pages (from-to)15438-15439
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number50
DOIs
StatePublished - Dec 19 2007

All Science Journal Classification (ASJC) codes

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

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