Hidden Boron Catalysis: A Cautionary Tale on TMEDA Inhibition
Hidden boron catalysis plagues catalyzed hydroboration reactions, with the "catalyst" acting to mediate the decomposition of HBpin/HBcat to BH<sub>3</sub> which is the actual (hidden) catalyst. <i>N</i>,<i>N</i>,<i>N'</i>,<i>N</i>'-Tetramethylethylenediamine (TMEDA) has been used to identify hidden boron catalysis through trapping/inhibition. Kinetic analyses showed that TMEDA inhibition is only applicable below 60 °C and that other amine traps are likewise ineffective. Awareness of this temperature limitation reveals widespread hidden catalysis in previous methods and should limit future false negative tests.
Authors
- Laure Meyer
- Stephen P. Thomas (ORCID: https://orcid.org/0000-0001-8614-2947)
- Andrew D. Bage (ORCID: https://orcid.org/0000-0002-5067-6899)
- J. G. Macleod
Institutions
- University of Edinburgh (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-28
- DOI
- https://doi.org/10.1021/acs.orglett.4c03591
- Citations
- 10
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.50
Funders
- Royal Society
- Engineering and Physical Sciences Research Council
- Biotechnology and Biological Sciences Research Council