Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds

Angewandte Chemie
Melanie A ShortJennifer L Roizen

Abstract

Masked alcohols are particularly appealing as directing groups because of the ubiquity of hydroxy groups in organic small molecules. Herein, we disclose a general strategy for aliphatic γ-C(sp3 )-H functionalization guided by a masked alcohol. Specifically, we determine that sulfamate ester derived nitrogen-centered radicals mediate 1,6-hydrogen-atom transfer (HAT) processes to guide γ-C(sp3 )-H chlorination. This reaction proceeds through a light-initiated radical chain-propagation process and is capable of installing chlorine atoms at primary, secondary, and tertiary centers.

References

Feb 2, 1977·Journal of the American Chemical Society·R BreslowR Kaleya
Nov 3, 2005·Journal of the American Chemical Society·Benjamin H Brodsky, J Du Bois
Mar 23, 2007·Nature·Robert G Bergman
Oct 16, 2007·Organic Letters·Joshua V RuppelX Peter Zhang
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
May 17, 2008·Journal of the American Chemical Society·Ke ChenPhil S Baran
Jul 24, 2008·Chemical Society Reviews·Samir Z Zard
Nov 26, 2009·Angewandte Chemie·Ke ChenPhil S Baran
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Sep 3, 2010·Journal of the American Chemical Society·Wei Liu, John T Groves
Oct 12, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Florence ColletPhilippe Dauban
Feb 8, 2011·Chemical Society Reviews·Will R Gutekunst, Phil S Baran
Oct 25, 2011·Accounts of Chemical Research·Tobias BrücklPhil S Baran
Feb 22, 2012·Science·M Christina White
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 4, 2013·Angewandte Chemie·Jennifer L RoizenJ Du Bois
May 2, 2014·Organic & Biomolecular Chemistry·Shunsuke Chiba, Hui Chen
Oct 28, 2014·Chemistry : a European Journal·Malek NechabMichèle P Bertrand
Apr 9, 2015·Organic Letters·Qixue Qin, Shouyun Yu
May 29, 2015·Angewandte Chemie·Claudio Martínez, Kilian Muñiz
Jun 5, 2015·Accounts of Chemical Research·Wei Liu, John T Groves
Oct 29, 2015·Chemical Society Reviews·Tim CernakShane W Krska
Nov 21, 2015·Nature Chemistry·Shauna M ParadineM Christina White
Dec 17, 2015·Chemical Science·Megan A Cismesia, Tehshik P Yoon
Dec 24, 2015·Journal of the American Chemical Society·Ryan K QuinnErik J Alexanian
Apr 28, 2016·Chemical Society Reviews·Tao Xiong, Qian Zhang
Jul 8, 2016·Angewandte Chemie·Ethan A WappesDavid A Nagib
Nov 30, 2016·Angewandte Chemie·Tao LiuJin-Quan Yu
Dec 10, 2016·Journal of the American Chemical Society·Satobhisha MukherjeeFrank Glorius
Mar 4, 2017·Organic Letters·Jun Ozawa, Motomu Kanai
Apr 11, 2017·Journal of the American Chemical Society·Ru-Yi ZhuJin-Quan Yu
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu
Jul 26, 2017·Journal of the American Chemical Society·Ethan A WappesDavid A Nagib
Oct 13, 2017·Journal of the American Chemical Society·Dian-Feng ChenTomislav Rovis

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Citations

Apr 10, 2018·Chemical Science·Shyam SathyamoorthiRichard N Zare
Aug 8, 2018·Angewandte Chemie·Christina G Na, Erik J Alexanian
Sep 7, 2018·Chemistry : a European Journal·Estefanía Del CastilloKilian Muñiz
Apr 14, 2019·Chemistry : a European Journal·Quan-Qing ZhaoWen-Jing Xiao
Sep 14, 2019·Chemical Communications : Chem Comm·Kensuke KiyokawaSatoshi Minakata
Feb 6, 2020·Chemistry, an Asian Journal·Gautam KumarIndranil Chatterjee
Jun 14, 2018·Chemical Science·Ethan A WappesDavid A Nagib
Apr 19, 2019·Chemical Science·Leah M StatemanDavid A Nagib
Feb 19, 2019·Chemical Science·Zuxiao ZhangDavid A Nagib
Jan 5, 2021·Chemical Communications : Chem Comm·Samuel D GriggsStephen P Marsden
Jul 15, 2020·The Journal of Organic Chemistry·Silvia GaspaLidia De Luca
Jan 23, 2021·Angewandte Chemie·Alexander FawcettJohn F Hartwig
Apr 23, 2021·Organic & Biomolecular Chemistry·Yanru LiYoichiro Kuninobu
Jan 31, 2020·Chemical Science·Andrew D ChenDavid A Nagib
Nov 8, 2019·Chemical Science·Melanie A ShortJennifer L Roizen
Aug 23, 2019·Organic Letters·J Miles BlackburnJennifer L Roizen
Nov 8, 2019·Journal of the American Chemical Society·Atanu ModakSilas P Cook
Feb 20, 2019·The Journal of Organic Chemistry·Suraj K Ayer, J L Roizen
Feb 15, 2018·Organic Letters·Hiromichi EgamiYoshitaka Hamashima
Nov 23, 2019·Journal of the American Chemical Society·Xiaojun ZengWei Liu
May 6, 2019·Organic Letters·Shengzong LiangGerald B Hammond
Jun 28, 2019·The Journal of Organic Chemistry·Makafui GasonooSébastien Laulhé
Nov 12, 2020·Organic Letters·Yanshuo ZhuWei Yu
Jul 18, 2019·Organic Letters·Anastasia L G KanegusukuJennifer L Roizen
Sep 13, 2019·The Journal of Organic Chemistry·Kohki M NakafukuDavid A Nagib
Aug 1, 2018·Organic Letters·Justin Y SuSarah E Reisman
Jan 14, 2020·Organic Letters·Anand H Shinde, Shyam Sathyamoorthi

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