Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds.

Journal of the American Chemical Society
Sung-Eun SuhShannon S Stahl

Abstract

Site selectivity represents a key challenge for non-directed C-H functionalization, even when the C-H bond is intrinsically reactive. Here, we report a copper-catalyzed method for benzylic C-H azidation of diverse molecules. Experimental and density functional theory studies suggest the benzyl radical reacts with a CuII-azide species via a radical-polar crossover pathway. Comparison of this method with other C-H azidation methods highlights its unique site selectivity, and conversions of the benzyl azide products into amine, triazole, tetrazole, and pyrrole functional groups highlight the broad utility of this method for target molecule synthesis and medicinal chemistry.

References

Mar 10, 2005·The New England Journal of Medicine·John C LaRosaUNKNOWN Treating to New Targets (TNT) Investigators
Aug 16, 2005·Angewandte Chemie·Stefan BräseViktor Zimmermann
Nov 18, 2005·The New England Journal of Medicine·Nazzareno GalièUNKNOWN Sildenafil Use in Pulmonary Arterial Hypertension (SUPER) Study Group
Aug 15, 2006·Analytical and Bioanalytical Chemistry·Aaron M PeckMichele M Schantz
Feb 14, 2009·The New England Journal of Medicine·Stefan H HohnloserUNKNOWN ATHENA Investigators
Oct 1, 2009·Nature Chemistry·Erik M Stang, M Christina White
Mar 18, 2011·Angewandte Chemie·Timothy Newhouse, Phil S Baran
Mar 24, 2012·Accounts of Chemical Research·Afaf H El-Sagheer, Tom Brown
Jun 19, 2014·Journal of the American Chemical Society·Eun Sil JangTimothy H Warren
Jan 13, 2015·Chemistry : a European Journal·Konstantin L IvanovMikhail Ya Melnikov
Apr 15, 2015·Journal of the American Chemical Society·Xiongyi HuangJohn T Groves
Oct 29, 2015·Chemical Society Reviews·Tim CernakShane W Krska
Jun 14, 2016·ACS Central Science·John F Hartwig, Matthew A Larsen
Aug 1, 2016·Bioorganic & Medicinal Chemistry Letters·Yasodakrishna SajjaLingaiah Nagarapu
Nov 2, 2016·ACS Central Science·Rashad R KarimovJohn F Hartwig
Mar 28, 2017·European Journal of Organic Chemistry·Monalisa Goswami, Bas de Bruin
Jun 1, 2017·Journal of the American Chemical Society·Wen ZhangGuosheng Liu
Sep 26, 2017·Accounts of Chemical Research·John F Hartwig
Mar 10, 2018·Journal of the American Chemical Society·Kaila A MargreyErik J Alexanian
May 2, 2018·Nature Chemistry·Joseph R ClarkM Christina White
Apr 17, 2019·The New England Journal of Medicine·Vlado PerkovicUNKNOWN CREDENCE Trial Investigators
Nov 7, 2019·Journal of the American Chemical Society·Lalita TanwarTobias Ritter

❮ Previous
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Citations

Oct 1, 2020·Chemical Communications : Chem Comm·Shuai LiuYannick Landais
Aug 15, 2020·Chemistry, an Asian Journal·Upma GulatiJoydev K Laha
Oct 21, 2020·Angewandte Chemie·Zhong-Wei HouHai-Chao Xu
Feb 27, 2021·Chemical Reviews·Paramasivam SivaguruXihe Bi
Apr 8, 2021·Nature Communications·Qing-Yuan MengArmido Studer
May 27, 2021·The Journal of Organic Chemistry·Masahiko Seki, Yusuke Takahashi
Jun 25, 2021·Chemical Science·Tjark H MeyerLutz Ackermann
Jul 24, 2021·Journal of the American Chemical Society·Wen LiuXiaoming Feng
Jul 27, 2021·Organic & Biomolecular Chemistry·Huifang LaiDaijun Zha
Aug 3, 2021·Journal of the American Chemical Society·Ming-Ming WangJerome Waser
Aug 11, 2021·Chemical Communications : Chem Comm·Masatoshi ShibuyaYoshihiko Yamamoto
Sep 18, 2020·Journal of the American Chemical Society·Linbin NiuAiwen Lei
Sep 1, 2021·Journal of the American Chemical Society·Si-Jie ChenShannon S Stahl
Sep 25, 2021·Journal of the American Chemical Society·Craig S DayJohn F Hartwig
Sep 8, 2021·Chemical Communications : Chem Comm·Long ZhengYongquan Ning
Sep 14, 2021·Nature·Ala BunescuMatthew J Gaunt
Nov 11, 2021·Organic Letters·Kaikai WangHongli Bao

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