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Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones

Authors :
Aspin, Sam
López-Suárez, Laura
Larini, Paolo
Goutierre, Anne-Sophie
Jazzar, Rodolphe
Baudoin, Olivier
Source :
Organic Letters; 20240101, Issue: Preprints
Publication Year :
2024

Abstract

Silyl ketene acetals are shown to be competent nucleophiles in Pd-catalyzed migrative C(sp3)–H arylations. Compared to the parent ester lithium enolates, they possess decreased reactivity but enhanced chemoselectivity. This behavior was exploited through the synthesis of valuable benzo-fused δ-lactones such as 1-isochromanones and dihydrocoumarins.

Details

Language :
English
ISSN :
15237060 and 15237052
Issue :
Preprints
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs31083325
Full Text :
https://doi.org/10.1021/ol402398s