Photoredox-Controlled Mono- and Di-Multifluoroarylation of C(sp3 )-H Bonds with Aryl Fluorides

Angewandte Chemie
Jin XieA Stephen K Hashmi

Abstract

A controllable mono- and di-multifluoroarylation of acyclic and cyclic N-aryl amines with aryl fluorides by photocatalyzed dual C(sp3 )-H/C(sp2 )-F functionalization has been developed, providing new access to a wide array of valuable α-fluoroarylated amines. In addition, the one-pot consecutive hetero-di-multifluoroarylation of N-aryl pyrrolidines and N,N-dimethylanilines was achieved with high to excellent diastereoselectivity. This new defluorinative C(sp3 )-C(sp2 ) coupling is distinguished by a broad scope, good regioselectivity, and mild conditions as well as gram-scale and late-stage applicability, and thus constitutes a significant advance in the arylation of unactivated C(sp3 )-H bonds with aryl fluorides.

References

Apr 27, 2001·Chemistry : a European Journal·A Studer
Feb 13, 2003·Journal of the American Chemical Society·Young Mi Kim, Shu Yu
Mar 5, 2004·Journal of the American Chemical Society·Jason D SlinkerGeorge G Malliaras
May 7, 2005·The Journal of Organic Chemistry·Gary W DombrowskiIan R Gould
Jan 10, 2008·Journal of the American Chemical Society·Hien-Quang Do, Olafs Daugulis
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Apr 1, 2009·Chemical Reviews·Hideki Amii, Kenji Uneyama
Aug 14, 2010·The Journal of Organic Chemistry·Matthew R CargillGabrielle Nelles
Oct 26, 2011·Journal of the American Chemical Society·Mamoru TobisuNaoto Chatani
Feb 5, 2014·Journal of the American Chemical Society·Hanchu HuangYiyun Chen
Feb 20, 2014·Journal of the American Chemical Society·Sameera M SenaweeraJimmie D Weaver
Apr 10, 2014·Journal of the American Chemical Society·Zhiwei Zuo, David W C MacMillan
Apr 30, 2014·Angewandte Chemie·Bertrand Schweitzer-ChaputMartin Klussmann
Sep 18, 2014·Journal of the American Chemical Society·Simon B LangJon A Tunge
Oct 31, 2014·The Journal of Organic Chemistry·James J DouglasCorey R J Stephenson
Aug 4, 2015·Chemical Science·Christopher K Prier, David W C MacMillan
Oct 16, 2015·Angewandte Chemie·Armido Studer, Dennis P Curran
Dec 10, 2015·Journal of the American Chemical Society·Xacobe C CambeiroIgor Larrosa
Feb 19, 2016·Journal of the American Chemical Society·Sameera Senaweera, Jimmie D Weaver
Apr 21, 2016·Chemical Communications : Chem Comm·Long HuangA Stephen K Hashmi
Oct 19, 2016·Accounts of Chemical Research·Amandeep Arora, Jimmie D Weaver
Jan 7, 2017·Chemical Science·Derek T Ahneman, Abigail G Doyle
Dec 1, 2015·Chemical Science·A SinghJ D Weaver

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Citations

Jul 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kohei MatsuzakiNorio Shibata
Feb 16, 2018·Angewandte Chemie·Nengneng ZhouChengjian Zhu
Jul 18, 2019·Chemical Communications : Chem Comm·Dawei CaoChao-Jun Li
May 17, 2019·Chemistry : a European Journal·Yangyang YangA Stephen K Hashmi
Jun 20, 2019·Chemistry : a European Journal·Massimo BrochettaDebabrata Maiti
Sep 12, 2019·Angewandte Chemie·Yueyue MaJinxing Ye
Jan 9, 2020·Organic & Biomolecular Chemistry·Milanpreet Kaur, Jeffrey F Van Humbeck
Jul 30, 2019·Angewandte Chemie·Pravas DoluiDebabrata Maiti
Aug 29, 2019·Chemical Communications : Chem Comm·Junlei WangWujiong Xia
Sep 26, 2017·Chemistry : a European Journal·Maria V IvanovaThomas Poisson
Apr 20, 2018·Chemical Communications : Chem Comm·Thomas P NichollsAlex C Bissember
Nov 23, 2017·Chemical Science·Lan-Gui Xie, Darren J Dixon
Aug 28, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrey SmolobochkinDenis Mishchenko
Oct 13, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Andrea GualandiPier Giorgio Cozzi
Jan 23, 2021·Angewandte Chemie·Xiang Sun, Tobias Ritter
Feb 1, 2018·The Journal of Organic Chemistry·Jie LiPatrick J Walsh
Jan 18, 2019·Journal of the American Chemical Society·Suhong Kim, F Dean Toste
Feb 14, 2020·Organic Letters·Peng-Ju XiaHua Yang
Nov 15, 2018·Journal of the American Chemical Society·Sonal Priya, Jimmie D Weaver
Jan 6, 2018·Organic Letters·Daria KurandinaVladimir Gevorgyan
Nov 15, 2017·Organic Letters·Jian ChengChengjian Zhu
Jan 27, 2019·Journal of the American Chemical Society·Weipeng LiChengjian Zhu
Aug 25, 2017·Journal of the American Chemical Society·Mohammad B KhaledJimmie D Weaver
May 9, 2019·The Journal of Organic Chemistry·Junlei WangWujiong Xia
Oct 30, 2021·Chemical Communications : Chem Comm·Junlei WangHongqing Li
Nov 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lei Zhou

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