Site selective hydrogen/metal exchange: Competition and cooperation between superbases and neighboring groups

Manfred Schlosser, Ferenc Faigl, Livia Franzini, Hervé Geneste, Georges Katsoulos, Guo fu Zhong

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

The appropriate choice of a metalating reagent is the key to the optional deprotonation of benzylamine derivatives at a position adjacent to the substituent or the nitrogen bearing side chain or even at the benzylic a-position of the latter. Subsequent reaction with suitable electrophiles followed by cyclization affords heterocyclic products such as isoquinolines and isoindolones. - Immediately when generated, some organometallic intermediates can undergo a rapid second hydrogen/metal exchange process. However, dimetalation is only kinetically, not thermodynamically favored as a careful investigation of typical cases has revealed. Moreover, it can be avoided if the donor capacity of the solvent or the polarity of the metalating reagent is increased. - Allylic organopotassium compounds exhibit intriguing stereopreferences. This pecularity has been exploited in a number of very simple sesquiterpene syntheses.

Original languageEnglish
Pages (from-to)1439-1446
Number of pages8
JournalPure and Applied Chemistry
Volume66
Issue number7
DOIs
Publication statusPublished - Jan 1 1994

    Fingerprint

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this