Exploiting deep eutectic solvents and organolithium reagent partnerships: chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions

Cristian Vidal, Joaquín García-Álvarez, Alberto Hernán-Gómez, Alan R. Kennedy, Eva Hevia

Research output: Contribution to journalArticle

63 Citations (Scopus)
9 Downloads (Pure)

Abstract

Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, biorenewable deep eutectic solvents (DESs) at room temperature and in the presence of air, establishing a novel and sustainable access to amines. Improving on existing methods, this approach proceeds in the absence of additives; occurs without competitive enolization, reduction or coupling processes; and reactions were completed in seconds. Comparing RLi reactivities in DESs with those observed in pure glycerol or THF suggests a kinetic anionic activation of the alkylating reagents occurs, favoring nucleophilic addition over competitive hydrolysis.
Original languageEnglish
Pages (from-to)16145-16148
Number of pages5
JournalAngewandte Chemie International Edition
Volume55
Issue number52
Early online date28 Nov 2016
DOIs
Publication statusPublished - 23 Dec 2016

Keywords

  • organolithium chemistry
  • imines
  • organolithium reagents
  • quinolines
  • chemoselective addition
  • deep eutectic solvents
  • biorenewable
  • green chemistry
  • salt activation

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