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. 2022 Nov 4;87(21):14731-14737.
doi: 10.1021/acs.joc.2c02048. Epub 2022 Oct 18.

Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides

Zhensheng You  1 , Yusuke Masuda  2   1 , Tomohiro Iwai  1 , Kosuke Higashida  2   1 , Masaya Sawamura  2   1
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Free article

Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides

Zhensheng You et al. J Org Chem. .
Free article

Abstract

A Ni-catalyzed cross-coupling reaction between aryl fluorides and dialkyl phosphonates [HP(O)(OR)2] (R = secondary alkyl groups) in the presence of potassium tert-butoxide as a base is reported. The reaction converted various aryl fluorides into the corresponding aryl phosphonates even when electron-donating substituents were present on the aromatic ring. The combined experimental and computational studies suggested Ni-K+ cooperative action of a Ni(0) complex chelated with a strongly electron-donating ion-bridged dimeric phosphite ligand system [P(OR)2O-K+]2 that facilitates turnover-limiting C-F bond oxidative addition of aryl fluorides.

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