Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides

You, Zhensheng; Masuda, Yusuke; Iwai, Tomohiro; Higashida, Kosuke; Sawamura, Masaya

Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides

You, Zhensheng; Masuda, Yusuke; Iwai, Tomohiro et al.

Journal of organic chemistry, 2023, 87(21), 14731-14737

Permalink : https://hdl.handle.net/2115/90676

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アクセス権	open access
URI	https://hdl.handle.net/2115/90676
タイトル	Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides
著者	You, Zhensheng ; Masuda, Yusuke ; Iwai, Tomohiro ; Higashida, Kosuke ; Sawamura, Masaya
著者名 You, Zhensheng
e-Rad_Researcher 20822307 著者名 Masuda, Yusuke
著者名 Iwai, Tomohiro
e-Rad_Researcher 20845466 著者名 Higashida, Kosuke
e-Rad_Researcher 40202105 著者名 Sawamura, Masaya
言語	英語
発行日	2023-11-09
出版者	American Chemical Society
収録物名	Journal of organic chemistry
巻(号)	87(21)
ページ	14731-14737
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	This document is the Accepted Manuscript version of a Published Work that appeared in final form in [JournalTitle], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-BEB28BHKFETDERJXCABA.
PISSN	0022-3263
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1021/acs.joc.2c02048