Visible-Light-Promoted Dearomative Fluoroalkylation of β-Naphthols through Intermolecular Charge Transfer

Angewandte Chemie
Quanping GuoZhaoqing Xu

Abstract

The first visible-light-promoted dearomative fluoroalkylation of β-naphthols was realized without the assistance of any transition-metal catalysts or external photosensitizers. Inexpensive fluoroalkyl iodides were directly used as efficient fluoroalkylation reagents under very mild reaction conditions. The scope of this process was found to be general and broad, and both trifluoromethyl and perfluoroalkyl groups (-C4 F9 , -C6 F13 , and -C8 F17 ) were installed in excellent yields. Preliminary mechanistic studies suggest that visible-light-promoted intermolecular charge transfer within the naphtholate-fluoroalkyl iodide electron donor-acceptor (EDA) complex induces a single electron transfer in the absence of photocatalysts.

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Citations

Jun 23, 2018·Chemistry : a European Journal·Yuan-Zheng ChengShu-Li You
Sep 6, 2018·Organic & Biomolecular Chemistry·Beatriz LantañoAl Postigo
Apr 12, 2019·Chemistry : a European Journal·Michael J JamesFrank Glorius
Sep 27, 2019·Chemical Communications : Chem Comm·Erlin ZhuChun-Yang He
Jan 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wen-Wen XuChun-Yang He
May 28, 2020·European Journal of Organic Chemistry·Mikiko Okumura, David Sarlah
Apr 24, 2021·Beilstein Journal of Organic Chemistry·Zhonglie YangJiahong Li
Aug 12, 2021·Organic & Biomolecular Chemistry·Hong-Wei Chen, Qin-Hua Song
Aug 14, 2019·Organic Letters·Liang ZhaoChun-Yang He
Mar 7, 2020·Journal of the American Chemical Society·Giacomo E M CrisenzaPaolo Melchiorre
Aug 7, 2019·Organic Letters·Savita B NagodeNamrata Rastogi
Dec 20, 2019·The Journal of Organic Chemistry·Heng LuAo Zhang
Sep 22, 2021·Organic & Biomolecular Chemistry·Meichen LiWei Deng
Aug 3, 2021·Chemistry : a European Journal·Beatrice BartolomeiMaurizio Prato

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