ArticleACS catalysis2024
Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.
Article in ACS catalysis, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Ligand Type Guided Keto-Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones.Angewandte Chemie (International ed. in English) · 2025Article
- Kinetic Modeling Enables Understanding of Off-Cycle Processes in Pd-Catalyzed Amination of Five-Membered Heteroaryl Halides.Journal of the American Chemical Society · 2024Article
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Authors and funding
5 authors.
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Abstract
The Suzuki-Miyaura cross-coupling (SMC) remains one of the most widely used transformations available to chemists. Recently, robust new conditions achieving rapid reactivity under homogeneous aprotic conditions enabled by the use of potassium trimethylsilanolate (TMSOK) as a base were reported. However, the strong inhibitory effect of TMSOK restricts the generality of such conditions. Moreover, the basic nature of TMSOK impedes the use of protic heterocycles as substrates, as these latter anionic species are even more potent catalyst inhibitors. Herein, we report a thorough mechanistic study of these novel SMC conditions. Halide salt additives were found to provide a dramatic rate acceleration and mitigate the inhibitory effect of TMSOK. NMR experiments revealed that this is largely achieved by impacting the unexpected formation of inactive [LnPd(Ar)(μ-OH)]
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