Alkali metal effects in trans-metal-trapping (TMT): comparing LiTMP with NaTMP in cooperative MTMP/Ga(CH2SiMe3)3 metalation reactions

Ross McLellan, Marina Uzelac, Leonie J. Bole, Jose Maria Gil-Negrete, David R. Armstrong, Alan R. Kennedy, Robert E. Mulvey, Eva Hevia

Research output: Contribution to journalArticle

2 Citations (Scopus)
22 Downloads (Pure)

Abstract

Stepwise metalation and trapping, so called trans-metal-trapping (TMT), of anisole is studied using LiTMP as base and Ga(CH2SiMe3)3 as trap. The isolated "trapped" intermediate is also assessed in C-C bond forming reactions, highlighting the inherent advantages and remaining challenges of this system. The same base trap mixture is found to metalate N-Me bonds of the diamines TMEDA and PMDETA. Comparative studies replacing LiTMP by NaTMP have found significant alkali metal effects on the extent of both base-trap cocomplexation and onward reactivities of TMT products.
Original languageEnglish
Pages (from-to)1207-1215
Number of pages9
JournalSynthesis
Volume51
Issue number05
DOIs
Publication statusPublished - 15 Jan 2019

Keywords

  • metalation
  • gallium trans metal trapping
  • carbanions
  • cooperative effects
  • lithium
  • sodium

Fingerprint Dive into the research topics of 'Alkali metal effects in trans-metal-trapping (TMT): comparing LiTMP with NaTMP in cooperative MTMP/Ga(CH<sub>2</sub>SiMe<sub>3</sub>)<sub>3</sub> metalation reactions'. Together they form a unique fingerprint.

Cite this