Lithium Enables Pd-Catalyzed 5-endo-dig Cyclization/Coupling of α‑Homopropargyl-β-ketoesters with Aryl Bromides and Triflates

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Authors
Bisek, Bartosz ORCID logo 0000-0003-2020-6068
Kochaniak, Katarzyna
Chaładaj, Wojciech ORCID logo 0000-0001-8143-3788
Date
2024
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ACS Publications
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Creative Commons License
Attribution 4.0 International
Abstract
Tight chelation of enolate by lithium alters the selectivity of tandem palladium-catalyzed cyclization/coupling of terminal α-homopropargyl-β-ketoesters with aryl halides. In the presence of LiOH, substituted cyclopentenes are preferentially formed via 5-endo-dig carbocyclization, in contrast to the 6-exo-dig oxocyclization exclusively observed in the absence of a hard, chelating metal center. The disclosed transformation, featuring mild conditions and broad functional group tolerance, can be applied for a variety of (hetero)aryl bromides as well as aryl and vinyl triflates.
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Citation
Cite this: Org. Lett. 2024, 26, 39, 8254–8259 ; https://doi.org/10.1021/acs.orglett.4c02846
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https://open.icm.edu.pl/handle/123456789/24984
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