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Regioselective Boracarboxylation of α-Substituted Vinyl Arenes

https://doi.org/10.1021/acs.organomet.2c00184

Knowlden, Steven W.; Popp, Brian V. (July 2022, Organometallics)

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Synthesis of Novel Multifunctional bora-Ibuprofen Derivatives

https://doi.org/10.3390/inorganics11020070

Abeysinghe, Randika T.; Ravenscroft, Alexis C.; Knowlden, Steven W.; Akhmedov, Novruz G.; Dolinar, Brian S.; Popp, Brian V. (February 2023, Inorganics)

A unique class of β-boron-functionalized non-steroidal anti-inflammatory compound (pinB-NSAID) was previously synthesized via copper-catalyzed 1,2-difunctionalization of the respective vinyl arene with CO2 and B2pin2 reagents. Here, pinacolylboron-functionalized ibuprofen (pinB-ibuprofen) was used as a model substrate to develop the conditions for pinacol deprotection and subsequent boron functionalization. Initial pinacol-boronic ester deprotection was achieved by transesterification with diethanolamine (DEA) from the boralactonate organic salt. The resulting DEA boronate adopts a spirocyclic boralactonate structure rather than a diazaborocane–DABO boronate structure. The subsequent acid-mediated hydrolysis of DEA and transesterification/transamination provided a diverse scope of new boron-containing ibuprofen derivatives.
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Synthesis of a Borylated Ibuprofen Derivative through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

https://doi.org/10.3791/64571

Knowlden, Steven W.; Abeysinghe, Randika T.; Swistok, Amanda D.; Ravenscroft, Alexis C.; Popp, Brian V. (January 2022, Journal of Visualized Experiments)

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Beneficial Effect of a Secondary Ligand on the Catalytic Difunctionalization of Vinyl Arenes with Boron and CO ₂

https://doi.org/10.1002/cctc.201901197

Perrone, Trina M.; Gregory, Amy S.; Knowlden, Steven W.; Ziemer, Natalie R.; Alsulami, Rabah N.; Petersen, Jeffrey L.; Popp, Brian V. (August 2019, ChemCatChem)

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