A General Pd-Catalyzed C2-H Arylation of Benzoxazoles with Highly Sterically Congested Aryl Chlorides Enabled by a Fittingly Tuned Ligand.

Autor: Song W; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong 999077, P. R. China., Tse MH; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong 999077, P. R. China., Lau YK; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong 999077, P. R. China., Cheung CW; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong 999077, P. R. China., Choy PY; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong 999077, P. R. China., Kwong FY; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong 999077, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Dec 06. Date of Electronic Publication: 2024 Dec 06.
DOI: 10.1021/acs.orglett.4c04117
Abstrakt: The benzoxazole core, featuring a sterically congested 2,6-disubstituted aryl fragment at the C2 position, exhibits exclusive three-dimensional structures that are essential for particular applications in material science and pharmaceutical development. Despite their importance, the synthesis of these compounds has posed challenges with an efficient preparation strategy still lacking. In this study, we introduced a new indolylphosphine ligand, PCy 2 -Man-phos , specifically designed to facilitate the C2-H arylation of benzoxazoles with sterically hindered aryl chlorides in general. The excellent functional group compatibility and rich arene substituted pattern enable the creation of highly decorated and sterically demanding 2-arylbenzoxazole frameworks, showing significant potential for diverse synthetic applications.
Databáze: MEDLINE