Dual C(sp3 )-H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions

Angewandte Chemie
Guo-Qiang XuPeng-Fei Xu

Abstract

Herein we describe a mild method for the dual C(sp3 )-H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3 )-H bonds.

References

May 31, 2002·Nature·Jay A Labinger, John E Bercaw
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Apr 12, 2008·Journal of Natural Medicines·Valery M Dembitsky
Sep 5, 2008·Journal of the American Chemical Society·Michael A IschayTehshik P Yoon
Nov 27, 2009·Chemical Reviews·Graham E Dobereiner, Robert H Crabtree
Jan 15, 2010·Journal of the American Chemical Society·Allison G CondieCorey R J Stephenson
Jan 30, 2010·Science·Mark S Chen, M Christina White
Jan 30, 2010·Chemical Society Reviews·Benito AlcaideCristina Aragoncillo
Jan 20, 2011·Angewandte Chemie·Thorsten Bach, Jörg P Hehn
Feb 24, 2011·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Mar 12, 2011·Chemical Reviews·Jongwook ChoiAlan S Goldman
Aug 13, 2011·Chemical Society Reviews·Charles M Marson
Aug 17, 2011·Journal of the American Chemical Society·Erik M Stang, M Christina White
Feb 3, 2012·Journal of the American Chemical Society·Yoshihiro MiyakeYoshiaki Nishibayashi
Jun 20, 2012·Angewandte Chemie·Jun Xuan, Wen-Jing Xiao
Aug 8, 2012·Chemical Society Reviews·Lei Shi, Wujiong Xia
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
May 4, 2013·Science·Elisabeth T Hennessy, Theodore A Betley
Jan 30, 2014·Journal of Medicinal Chemistry·Richard D TaylorAlastair D G Lawson
Feb 11, 2015·Journal of the American Chemical Society·Laura Ruiz EspeltTehshik P Yoon
May 8, 2015·Accounts of Chemical Research·Joel W Beatty, Corey R J Stephenson
Nov 14, 2015·Journal of the American Chemical Society·John F Hartwig
Feb 18, 2016·Nature·Joseph J TopczewskiMelanie S Sanford
Apr 21, 2016·Nature·Evan J HornPhil S Baran
Apr 28, 2016·Chemical Reviews·Markus D KärkäsCorey R J Stephenson
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Jan 1, 1996·Journal of Research of the National Institute of Standards and Technology·David G Watson
Dec 14, 2016·Journal of the American Chemical Society·Elango KumarasamyJ Sivaguru
Feb 1, 2017·Journal of the American Chemical Society·Shota KatoMotomu Kanai
Jul 8, 2017·Journal of the American Chemical Society·Jiannan ZhaoOhyun Kwon

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Citations

Sep 14, 2018·Chemical Communications : Chem Comm·Hongyu WangBo Tang
Jun 22, 2019·Organic & Biomolecular Chemistry·Zdravko DŽambaski, Bojan P BondŽić
Jan 7, 2020·Chemical Communications : Chem Comm·Fernando HerreraPedro Almendros
Apr 2, 2020·Nature Chemistry·Weijie ChenDaniel Seidel
Jan 15, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marianne B Haarr, Magne O Sydnes
Oct 24, 2019·The Journal of Organic Chemistry·Ji-Tao XuPeng-Fei Xu
Jun 23, 2020·The Journal of Organic Chemistry·Xiao-De AnJian Xiao
Sep 22, 2018·The Journal of Organic Chemistry·Jing GuoGui Lu

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