ArticleOrganic process research & development2019
Off-Cycle Processes in Pd-Catalyzed Cross-Coupling of Carboranes.
Article in Organic process research & development, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- A General Sonogashira-Type Strategy for Exopolyhedral B-C(sp) Bond Formation onOrganic letters · 2026Article
- Deciphering the Synchronization of Alternating Current Frequency with the Nickel Catalytic Cycle in Selective C-N Cross-Coupling.Journal of the American Chemical Society · 2025Article
- A Pd-catalyzed route to carborane-fused boron heterocycles.Chemical science · 2024Article
- Optoelectronic Response to the Fluor Ion Bond on 4-(4,4,5,5-Tetramethyl-1,3,2-dioxoborolan-2-yl)benzaldehyde.International journal of molecular sciences · 2024Article
- Electrochemical Cage Activation of Carboranes.Angewandte Chemie (International ed. in English) · 2022Review
- ElectrooxidativeChemical science · 2021Article
- Electrochemical B-H Nitrogenation: Access to Amino Acid and BODIPY-Labeled nido-Carboranes.Angewandte Chemie (International ed. in English) · 2021Article
- Expanding the Scope of Palladium-Catalyzed B - N Cross-Coupling Chemistry in Carboranes.Organometallics · 2020Article
- Carborane Guests for Cucurbit[7]uril Facilitate Strong Binding and On-Demand Removal.Journal of the American Chemical Society · 2020Article
- Oxidative Generation of Boron-Centered Radicals in Carboranes.Journal of the American Chemical Society · 2020Article
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Authors and funding
4 authors.
Funding
Abstract
Off-cycle processes in catalytic reactions can dramatically influence the outcome of the chemical transformation and affect its yield, selectivity, rate, and product distribution. While the generation of off-cycle intermediates can complicate reaction coordinate analyses or hamper catalytic efficiency, the generation of such species may also open new routes to unique chemical products. Recently, we reported the Pd-mediated functionalization of carboranes with a range of O-, N-, and C-based nucleophiles. By utilizing a Pd-based catalytic system supported by a biaryl phosphine ligand developed by Buchwald and co-workers, we discovered an off-cycle isomerization process ("cage-walking") that generates four regioisomeric products from a single halogenated boron cluster isomer. Here we describe how several off-cycle processes affect the regioisomer yield and distribution during Pd-catalyzed tandem cage-walking/cross-coupling. In particular, tuning the transmetallation step in the catalytic cycle allowed us to incorporate the cage-walking process into Pd-catalyzed cross-coupling of sterically unencumbered substrates, including cyanide. This work demonstrates the feasibility of using tandem cage-walking/cross-coupling as a unique low-temperature method for producing regioisomers of mono-substituted carboranes.
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