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

[thumbnail of McLellan-etal-Synthesis2018-Alkali-metal-effects-in-trans-metal-trapping-TMT]
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.

    ORCID iDs

    McLellan, Ross ORCID logoORCID: https://orcid.org/0000-0001-9700-0258, Uzelac, Marina ORCID logoORCID: https://orcid.org/0000-0002-5060-7017, Bole, Leonie J., Gil-Negrete, Jose Maria, Armstrong, David R., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Mulvey, Robert E. ORCID logoORCID: https://orcid.org/0000-0002-1015-2564 and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
    • Item type:Article
      ID code:66470
      Dates:
      Date
      Event
      15 January 2019
      Published
      5 December 2018
      Accepted
      Keywords:metalation, gallium trans metal trapping, carbanions, cooperative effects, lithium, sodium, Chemistry, Chemistry(all)
      Subjects:Science > Chemistry
      Department:Faculty of Science > Pure and Applied Chemistry
      Depositing user: Pure Administrator
      Date deposited:08 Jan 2019 10:06
      Last modified:10 May 2021 00:52
      Related URLs:
      URI:https://strathprints.strath.ac.uk/id/eprint/66470
    CORE (COnnecting REpositories)