Work

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

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02846

Authors: Bartosz Bisek, Katarzyna Kochaniak, Wojciech Chaładaj

Institutions: Institute of Organic Chemistry, Polish Academy of Sciences

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Narodowe Centrum Nauki