Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling | Zendy

Robert Szpera | Zendy; Patrick G. Isenegger | Zendy; Maxime Ghosez | Zendy; Natan J. W. Straathof | Zendy; Rosa Cookson | Zendy; David C. Blakemore | Zendy; Paul Richardson | Zendy; Véronique Gouverneur | Zendy

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Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling

Author(s) -

Robert Szpera,

Patrick G. Isenegger,

Maxime Ghosez,

Natan J. W. Straathof,

Rosa Cookson,

David C. Blakemore,

Paul Richardson,

Véronique Gouverneur

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02347

Subject(s) - chemistry , aryl , catalysis , toluene , palladium , alkyl , coupling reaction , functional group , combinatorial chemistry , compatibility (geochemistry) , coupling (piping) , organic chemistry , chemical engineering , mechanical engineering , polymer , engineering

Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst t BuBrettPhos Pd G3 and Cs 2 CO 3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and -poor (hetero)arenes. The method provides access to 18 F-labeled trifluoroethyl ethers by cross-coupling with [ 18 F]trifluoroethanol.

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