The direct arylation of allylic sp(3) C-H bonds via organic and photoredox catalysis

Nature
James D Cuthbertson, David W C MacMillan

Abstract

The direct functionalization of unactivated sp(3) C-H bonds is still one of the most challenging problems facing synthetic organic chemists. The appeal of such transformations derives from their capacity to facilitate the construction of complex organic molecules via the coupling of simple and otherwise inert building blocks, without introducing extraneous functional groups. Despite notable recent efforts, the establishment of general and mild strategies for the engagement of sp(3) C-H bonds in C-C bond forming reactions has proved difficult. Within this context, the discovery of chemical transformations that are able to directly functionalize allylic methyl, methylene and methine carbons in a catalytic manner is a priority. Although protocols for direct oxidation and amination of allylic C-H bonds (that is, C-H bonds where an adjacent carbon is involved in a C = C bond) have become widely established, the engagement of allylic substrates in C-C bond forming reactions has thus far required the use of pre-functionalized coupling partners. In particular, the direct arylation of non-functionalized allylic systems would enable access to a series of known pharmacophores (molecular features responsible for a drug's action), though a ...Continue Reading

References

Oct 10, 2001·Angewandte Chemie·Jason Eames, Michael Watkinson
Feb 1, 1996·Chemical Reviews·Barry M. Trost, David L. Van Vranken
Feb 19, 2002·Chemical Reviews·Mogens Johannsen, Karl Anker Jørgensen
Sep 3, 2009·Journal of the American Chemical Society·David A NagibDavid W C MacMillan
Jun 10, 2010·Chemical Society Reviews·Jagan M R Narayanam, Corey R J Stephenson
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Mar 30, 2013·Science·Michael T PirnotDavid W C MacMillan
Dec 18, 2013·Journal of the American Chemical Society·Katrine QvortrupDavid W C MacMillan
Mar 1, 2014·Science·Danielle M Schultz, Tehshik P Yoon
Mar 15, 2014·Organic Letters·Kelli A Ogawa, Andrew J Boydston

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Citations

Dec 15, 2015·Chembiochem : a European Journal of Chemical Biology·Joanne L PorterDavid L Ollis
Jan 30, 2016·Nature Communications·Zuyong DengJi-Chang Xiao
Jan 16, 2016·The Journal of Organic Chemistry·Huw M L Davies, Daniel Morton
Apr 9, 2016·Organic & Biomolecular Chemistry·Michael Gurry, Fawaz Aldabbagh
Aug 27, 2015·Nature·Jian Jin, David W C MacMillan
Apr 14, 2016·Chemical Reviews·Davide RavelliMaurizio Fagnoni
Aug 6, 2015·Organic & Biomolecular Chemistry·Ricardo A AngnesGerald B Hammond
Mar 6, 2015·Nature·James J Devery, Corey R J Stephenson
Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
Nov 8, 2016·Chemical Society Reviews·Nathaniel CorriganCyrille Boyer
Jun 9, 2016·The Journal of Organic Chemistry·Yang YuXin-Shan Ye
Jun 16, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Taye B Demissie, Jørn H Hansen
Jul 8, 2016·Journal of the American Chemical Society·Xiaoshen Ma, Seth B Herzon
Jul 6, 2016·The Journal of Organic Chemistry·Melissa ReckenthälerAxel G Griesbeck
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Sep 14, 2016·Journal of the American Chemical Society·Wenxin ChenGuigen Li
Dec 10, 2016·Journal of the American Chemical Society·Satobhisha MukherjeeFrank Glorius
Dec 15, 2016·Journal of the American Chemical Society·Wan Ru LeowXiaodong Chen
Jan 12, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Qixue QinShouyun Yu
Feb 1, 2017·Journal of the American Chemical Society·Shota KatoMotomu Kanai
Apr 1, 2017·Journal of the American Chemical Society·Xiaoshen MaSeth B Herzon
May 4, 2017·Chemistry : a European Journal·Keiichi YamadaIlhyong Ryu

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