Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

Angewandte Chemie
Maxim RatushnyyVladimir Gevorgyan

Abstract

A mild visible-light-induced Pd-catalyzed intramolecular C-H arylation of amides is reported. The method operates by cleavage of a C(sp2 )-O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.

References

Jun 25, 2004·Chemical Communications : Chem Comm·Yajun Wang, Frank Caruso
Jul 12, 2008·The Journal of Organic Chemistry·J Mikael Hillgren, Stephen P Marsden
Jan 27, 2009·Angewandte Chemie·Yi-Xia Jia, E Peter Kündig
Jun 24, 2010·Angewandte Chemie·Xiao-Feng WuMatthias Beller
Aug 7, 2010·The Journal of Organic Chemistry·Nina DeppermannWolfgang Maison
Sep 23, 2010·Journal of the American Chemical Society·Xiaoqiang ShenStephen L Buchwald
Nov 23, 2010·Chemical Reviews·Nicklas Selander, Kálmán J Szabó
Jan 6, 2011·Chemistry : a European Journal·Xiao-Feng WuMatthias Beller
May 11, 2012·Angewandte Chemie·Carin C C Johansson SeechurnVictor Snieckus
Jul 25, 2012·Nature Chemistry·Ana-Florina VoicaPhil S Baran
Aug 18, 2012·Chemical Society Reviews·Renato DalpozzoGiorgio Bencivenni
Jan 24, 2013·Organic Letters·Fanzhi Yang, Lutz Ackermann
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Nov 10, 2013·Beilstein Journal of Organic Chemistry·Klaus Speck, Thomas Magauer
Aug 27, 2014·Angewandte Chemie·Fanzhi YangLutz Ackermann
Sep 13, 2014·Chemistry : a European Journal·Carlos VilaBen L Feringa
Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Sep 14, 2016·Journal of the American Chemical Society·Samantha A GreenRyan A Shenvi
Feb 25, 2017·Organic Letters·Keshav RaghuvanshiLutz Ackermann
Aug 2, 2017·Chemical Society Reviews·Jin XieA Stephen K Hashmi
Aug 12, 2017·Chemical Society Reviews·Marvin Parasram, Vladimir Gevorgyan
Oct 11, 2017·Journal of the American Chemical Society·Marvin ParasramVladimir Gevorgyan
Nov 9, 2017·Journal of the American Chemical Society·Guang-Zu WangYao Fu
Jan 6, 2018·Organic Letters·Daria KurandinaVladimir Gevorgyan
Feb 6, 2018·Journal of the American Chemical Society·Padon ChuentragoolVladimir Gevorgyan
Apr 13, 2018·Angewandte Chemie·Zhiwei JiaoJianrong Steve Zhou
Apr 18, 2018·Journal of the American Chemical Society·Harshkumar H PatelMatthew S Sigman
May 15, 2018·Synthesis·Leah M StatemanDavid A Nagib
Aug 14, 2018·Journal of the American Chemical Society·José A CarmonaJosé M Lassaletta

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Citations

Oct 21, 2020·Nature Communications·Daeun KimSoon Hyeok Hong
Dec 15, 2020·Chemical Society Reviews·Nikita Kvasovs, Vladimir Gevorgyan
Oct 31, 2020·Chemistry : a European Journal·Risto Savela, Carolina Méndez-Gálvez
Jun 25, 2021·Chemical Science·Peter BellottiFrank Glorius
Dec 9, 2020·Journal of the American Chemical Society·Huong DauEva Harth
May 8, 2020·Journal of the American Chemical Society·Huan-Ming HuangFrank Glorius
Aug 26, 2021·Organic Letters·Krishnamoorthy MuralirajanMagnus Rueping
Oct 9, 2021·Chemical Reviews·Kelvin Pak Shing CheungVladimir Gevorgyan

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