Alkali Metal Effects in Trans-Metal-Trapping (TMT): Comparing LiTMP with NaTMP in Cooperative MTMP/Ga(CH 2 SiMe 3 ) 3 Metalation Reactions

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

Research output: Contribution to journalReview articlepeer-review

15 Citations (SciVal)

Abstract

Stepwise metalation and trapping, so called trans-metal-trapping (TMT), of anisole is studied using LiTMP as base and Ga(CH 2 SiMe 3 ) 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 metallate 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 (Germany)
Volume51
Issue number5
DOIs
Publication statusPublished - 15 Jan 2019

Bibliographical note

Funding Information:
We thank the European Research Council (ERC StG, MixMetApps) and the EPSRC (EP/N011384/1) for their generous sponsorship of this research. European Research Council (ERCStG, MixMetApps) Engineering and Physical Sciences Research Council (EP/N011384/1)

Funding

Merit Award, Royal Society Leverhulme Trust Senior Research Fellowship, GDCh Arfvedson Schlenk Prize, and a Humboldt Research Award. A Fellow of both the Royal Society of Edinburgh and Royal So ciety of Chemistry, he has published ap proaching 300 papers. We thank the European Research Council (ERC StG, MixMetApps) and the EPSRC (EP/N011384/1) for their generous sponsorship of this research.EuropeanResearchCouncil(ERCStG,MixMetApps)EngineeringandPhysicalSciencesResearchCouncil (EP/N011384/1)

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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