Light opens a new window for N-heterocyclic carbene catalysis.

Chemical Science
Jing LiuWen-Jing Xiao

Abstract

N-Heterocyclic carbenes (NHCs) are efficient Lewis basic catalysts for the umpolung of various polarized unsaturated compounds usually including aldehydes, imines, acyl chlorides and activated esters. NHC catalysis involving electron pair transfer steps has been extensively studied; however, NHC catalysis through single-electron transfer (SET) processes, despite having the potential to achieve chemical transformations of inert chemical bonds and using green reagents, has long been a challenging task in organic synthesis. In parallel, visible-light-induced photocatalysis and photoexcitation have been established as powerful tools to facilitate sustainable organic synthesis, as they enable the generation of various reactive radical intermediates under extremely mild conditions. Recently, a number of elegant visible-light-induced, NHC-catalyzed transformations were developed for accessing valuable organic compounds. As a result, this minireview will highlight the recent advances in this field.

References

Apr 14, 2005·Journal of the American Chemical Society·Alexander Arefolov, James S Panek
Apr 10, 2008·Angewandte Chemie·F Ekkehardt Hahn, Mareike C Jahnke
Oct 11, 2008·Angewandte Chemie·Joyram GuinArmido Studer
Jun 10, 2010·Chemical Society Reviews·Jagan M R Narayanam, Corey R J Stephenson
Jun 12, 2010·Bioorganic & Medicinal Chemistry Letters·Pradeep CherukuCarole A Bewley
Jan 20, 2011·Angewandte Chemie·Thorsten Bach, Jörg P Hehn
Mar 2, 2012·Chemical Society Reviews·Xavier Bugaut, Frank Glorius
Jun 20, 2012·Angewandte Chemie·Jun Xuan, Wen-Jing Xiao
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Oct 31, 2013·Organic & Biomolecular Chemistry·Xiang-Yu Chen, Song Ye
Mar 1, 2014·Science·Danielle M Schultz, Tehshik P Yoon
Mar 7, 2014·Chemistry : a European Journal·Matthew N HopkinsonFrank Glorius
Jun 27, 2014·Nature·Matthew N HopkinsonFrank Glorius
Feb 5, 2015·Journal of the American Chemical Society·Yuexia ZhangYonggui Robin Chi
Mar 19, 2015·Angewandte Chemie·Miguel Peña-LópezMatthias Beller
May 21, 2015·Chemical Reviews·Darrin M FlaniganTomislav Rovis
Aug 11, 2015·Journal of the American Chemical Society·Nicholas A White, Tomislav Rovis
Apr 14, 2016·Chemical Reviews·Davide RavelliMaurizio Fagnoni
Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Oct 21, 2016·Angewandte Chemie·Michael H Wang, Karl A Scheidt
Sep 28, 2017·Journal of the American Chemical Society·Miao-Miao LiWen-Jing Xiao
May 19, 2018·Angewandte Chemie·Quan-Quan ZhouWen-Jing Xiao
Feb 21, 2019·Journal of the American Chemical Society·Takuya IshiiHirohisa Ohmiya
Aug 27, 2019·Journal of the American Chemical Society·Takuya IshiiHirohisa Ohmiya
Dec 10, 2019·Angewandte Chemie·Andreas MavroskoufisMatthew N Hopkinson
Jan 23, 2020·Chemical Reviews·Qun ZhaoMichal Szostak
Jun 8, 2021·Chemical Science·Takuya IshiiHirohisa Ohmiya

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Citations

Jan 13, 2021·Organic Letters·Hai-Bin Yang, Dan-Hong Wan
Mar 25, 2021·Journal of the American Chemical Society·Kun Liu, Armido Studer
Apr 8, 2021·Nature Communications·Qing-Yuan MengArmido Studer
Oct 10, 2020·Chemistry : a European Journal·Qing-Zhu LiJun-Long Li
Nov 27, 2020·Chemical Communications : Chem Comm·Shilpa Barik, Akkattu T Biju
Jul 8, 2021·Accounts of Chemical Research·Xiaotian Qi, Yu Lan
May 16, 2021·Angewandte Chemie·Shun Wang, Burkhard König
Nov 17, 2021·Chemical Society Reviews·Yao WangYing-Feng Han
Nov 18, 2021·Organic Letters·Yuxing CaiYong Huang

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Methods Mentioned

BETA
acylation

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