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

McLellan, Ross and Uzelac, Marina and Bole, Leonie J. and Gil-Negrete, Jose Maria and Armstrong, David R. and Kennedy, Alan R. and Mulvey, Robert E. and Hevia, Eva (2019) Alkali metal effects in trans-metal-trapping (TMT) : comparing LiTMP with NaTMP in cooperative MTMP/Ga(CH2SiMe3)3 metalation reactions. Synthesis, 51 (05). pp. 1207-1215. ISSN 0039-7881

[img]
Preview
Text (McLellan-etal-Synthesis2018-Alkali-metal-effects-in-trans-metal-trapping-TMT)
McLellan_etal_Synthesis2018_Alkali_metal_effects_in_trans_metal_trapping_TMT.pdf
Final Published Version
License: Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 logo

Download (4MB)| Preview

    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.