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 (https://doi.org/10.1055/s-0037-1611646)

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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;
CORE (COnnecting REpositories)