Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange

Andreas D. Benischke, Lucile Anthore-Dalion, Guillaume Berionni, Paul Knochel

Research output: Contribution to journalArticlepeer-review

Abstract

Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu2LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at −50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 106-times higher rates, making it comparable to Br/Li exchange.

Original languageEnglish
Pages (from-to)16390-16394
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number51
DOIs
Publication statusPublished - 18 Dec 2017
Externally publishedYes

Keywords

  • 1,2-addition
  • acylation
  • halogen–lanthanum exchange
  • kinetic studies
  • lanthanum

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