ArticleJournal of the American Chemical Society2018
Elucidating the Role of the Boronic Esters in the Suzuki-Miyaura Reaction: Structural, Kinetic, and Computational Investigations.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 49 papers.
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Who cites it
49 citing papers in PubMed, 157 citations in OpenAlex.
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- Efficient and Rapid Arylation of NH₂-Unprotected Bromobisindole Ethanamines via Suzuki-Miyaura Coupling: Generating New Leads Against Leishmania.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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- Suzuki-Miyaura Cross-Couplings: Juxtaposing the Transmetalation of Arylboronic Acids and Alkylboranes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Rapid, Homogenous, B-Alkyl Suzuki-Miyaura Cross-Coupling of Boronic Esters.The Journal of organic chemistry · 2024Article
- Chemoselective Cu-Catalyzed Cross-Nucleophile Alkylarylation of Alkenes.ACS catalysis · 2024Article
- Revealing the Hidden Complexity and Reactivity of Palladacyclic Precatalysts: The P(ACS catalysis · 2024Article
- Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.ACS catalysis · 2024Article
- Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.Nature communications · 2024Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The Suzuki-Miyaura reaction is the most practiced palladium-catalyzed, cross-coupling reaction because of its broad applicability, low toxicity of the metal (B), and the wide variety of commercially available boron substrates. A wide variety of boronic acids and esters, each with different properties, have been developed for this process. Despite the popularity of the Suzuki-Miyaura reaction, the precise manner in which the organic fragment is transferred from boron to palladium has remained elusive for these reagents. Herein, we report the observation and characterization of pretransmetalation intermediates generated from a variety of commonly employed boronic esters. The ability to confirm the intermediacy of pretransmetalation intermediates provided the opportunity to clarify mechanistic aspects of the transfer of the organic moiety from boron to palladium in the key transmetalation step. A series of structural, kinetic, and computational investigations revealed that boronic esters can transmetalate directly without prior hydrolysis. Furthermore, depending on the boronic ester employed, significant rate enhancements for the transfer of the B-aryl groups were observed. Overall, two critical features were identified that enable the transfer of the organic fragment from boron to palladium: (1) the ability to create an empty coordination site on the palladium atom and (2) the nucleophilic character of the ipso carbon bound to boron. Both of these features ultimately relate to the electron density of the oxygen atoms in the boronic ester.
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Registered trials
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