Development of N,N-bis(perfluoroalkanesulfonyl)squaramides as new strong Brønsted acids and their application to organic reactions

Cheol-Hong Cheon, Hisashi Yamamoto

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

New strong Brønsted acids derived from a squaric acid scaffold bearing different perfluoroalkanesulfonyl groups have been developed and applied to several organic reactions. These squaramides are bench-stable and exhibit much higher reactivities in several organic reactions than squaric acid itself. N,N-Bis(trifluoromethanesulfonyl)squaramide 2a was applied to the Mukaiyama aldol reaction and Mukaiyama Michael reaction. Mechanistic studies revealed that the Brønsted acid might be the predominant catalyst through direct protonation of carbonyl compound by the acid itself rather than the silylated Brønsted acid. The utility of this acid 2a was further extended to Hosomi-Sakurai allylation of aldehydes and a carbonyl-ene reaction. Furthermore, other squaramides 2b and c bearing longer perfluoroalkyl chains have been developed, which are also bench-stable and displayed similar reactivities with squaramide 2a in several organic reactions.

Original languageEnglish
Pages (from-to)4257-4264
Number of pages8
JournalTetrahedron
Volume66
Issue number24
DOIs
Publication statusPublished - 2010 Jun 12
Externally publishedYes

Keywords

  • Brønsted acid catalysis
  • Carbonyl activation
  • Perfluoroalkanesulfonyl
  • Squaramide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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