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 language | English |
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Pages (from-to) | 1207-1215 |
Number of pages | 9 |
Journal | Synthesis (Germany) |
Volume | 51 |
Issue number | 5 |
DOIs | |
Publication status | Published - 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