ArticleACS catalysis2021
The Stereochemical Course of Pd-Catalyzed Suzuki Reactions Using Primary Alkyltrifluoroborate Nucleophiles.
Article in ACS catalysis, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Stereospecific cross-coupling reactions: Programmed assembly of chiral molecules by reaction of chiral reagents.Science advances · 2025Review
- Rapid, Homogenous, B-Alkyl Suzuki-Miyaura Cross-Coupling of Boronic Esters.The Journal of organic chemistry · 2024Article
- Enantiospecific cross-coupling of cyclic alkyl sulfones.Nature chemistry · 2024Article
- Reactions of Benzylboronate Nucleophiles.Synthesis · 2023Article
- Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.Journal of the American Chemical Society · 2022Article
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5 authors.
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Abstract
Using deuterium-labeled stereochemical probes, we show that primary alkyltrifluoroborate nucleophiles undergo transmetalation to palladium exclusively via a stereoretentive pathway and that the resulting stereospecificity is broadly independent of electronic and steric effects. This stands in stark contrast to the stereochemical course of transmetalation for secondary alkyltrifluoroborates, which varies between net stereoretention and net stereoinversion depending upon the electronic properties of the supporting phosphine ligand, the electronic properties of the aryl electrophile, and the steric properties of the alkylboron nucleophile. In this study, we additionally show that the stereochemical course of transmetalation for secondary alkylboron reagents can be under reagent steric control, while no such steric control exists for analogous primary alkylboron nucleophiles. The combined study reveals fundamental mechanistic differences between transmetalations of primary and secondary alkylboron reagents in Pd-catalyzed Suzuki reactions.
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