ArticleNature communications2024
Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Direct-inject liquid-chromatography enables an autonomous continuous preferential crystallization platform.Chemical science · 2026Article
- Frugal Sampling Strategies for Navigating Complex Reaction Spaces.Organic process research & development · 2026Article
- Suzuki-Miyaura Cross-Couplings: Juxtaposing the Transmetalation of Arylboronic Acids and Alkylboranes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.ACS catalysis · 2024Article
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Authors and funding
4 authors.
Funding
Abstract
The Suzuki-Miyaura coupling is a widely used C-C bond forming reaction. Numerous mechanistic studies have enabled the use of low catalyst loadings and broad functional group tolerance. However, the dominant mode of transmetalation remains controversial and likely depends on the conditions employed. Herein we detail a mechanistic study of the palladium-catalyzed Suzuki-Miyaura coupling under biphasic conditions. The use of phase transfer catalysts results in a remarkable 12-fold rate enhancement in the targeted system. A shift from an oxo-palladium based transmetalation to a boronate-based pathway lies at the root of this activity. Furthermore, a study of the impact of different water loadings reveals reducing the proportion of the aqueous phase increases the reaction rate, contrary to reaction conditions typically employed in the literature. The importance of these findings is highlighted by achieving an exceptionally broad substrate scope with benzylic electrophiles using a 10-fold reduction in catalyst loading relative to literature precedent.
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