Selective C(sp3 )-H and C(sp2 )-H Fluorination of Alcohols Using Practical Auxiliaries

Angewandte Chemie
Yang-Jie MaoDan-Qian Xu

Abstract

Selective introduction of fluorine into molecules by the cleavage of inert C-H bonds is of central academic and synthetic interest, yet remains challenging. Given the central role of alcohols in organic chemistry as the most ubiquitous building blocks, a versatile and selective C(sp3 )-H and C(sp2 )-H fluorination of simple alcohols, enabled by novel designed exo-directing groups, is described. C(sp2 )-H bond fluorination was achieved by using a simple acetone oxime as auxiliary, whereas a new, modular and easily accessible bidentate auxiliary was developed for the efficient and site-selective fluorination of various primary methyl, methylene, and benzylic C(sp3 )-H bonds. Fluorinated alcohols can readily be accessed by the removal of auxiliaries, and significantly expands the synthetic prospect of the present procedure.

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Citations

Sep 5, 2019·Angewandte Chemie·Conghui TangDavid Sarlah
Feb 14, 2019·Angewandte Chemie·Robert SzperaVéronique Gouverneur
Nov 16, 2019·Chemical Communications : Chem Comm·Yang-Jie MaoDan-Qian Xu
Oct 11, 2019·Beilstein Journal of Organic Chemistry·Xiaowei LiDayong Shi
Feb 13, 2020·Angewandte Chemie·Guoqin XiaJin-Quan Yu
Aug 25, 2020·Organic & Biomolecular Chemistry·Xue XiongDan-Qian Xu
May 31, 2019·Chemical Communications : Chem Comm·Bing-Xin WangDan-Qian Xu
Dec 20, 2018·Chemical Communications : Chem Comm·Yang-Jie MaoDan-Qian Xu
Dec 24, 2020·Chemical Communications : Chem Comm·Qiu-Zi WuDan-Qian Xu
May 7, 2021·Chemical Communications : Chem Comm·Qiuzi WuDan-Qian Xu
Jul 23, 2020·Journal of the American Chemical Society·William G Whitehurst, Matthew J Gaunt
Dec 16, 2019·Chemical Science·Emily N PinterSilas P Cook
Jul 23, 2021·Chemical Communications : Chem Comm·Hong-Yan HaoDan-Qian Xu
May 5, 2020·Journal of the American Chemical Society·Yan-Qiao ChenJin-Quan Yu
Sep 15, 2019·Journal of the American Chemical Society·Keita TanakaJin-Quan Yu
Mar 4, 2020·Organic Letters·Hong-Yan HaoDan-Qian Xu
Dec 23, 2020·Organic Letters·Quan GouXing Zhang
Aug 14, 2019·Journal of the American Chemical Society·Elizabeth A MeucciMelanie S Sanford
Oct 26, 2021·Chemical Communications : Chem Comm·Sumeet Ranjan SahooDebabrata Maiti
Feb 4, 2022·Chemical Communications : Chem Comm·Srinivasarao Arulananda BabuRadha Tomar

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