Copper-Catalyzed Selective 1,2-Dialkylation of N-Heteroarenes via a Radical Addition/Reduction Process: Application for the Construction of Alkylated Dihydroazaarenes Derivatives

The Journal of Organic Chemistry
Qiu SunChao-Guo Yan

Abstract

A highly efficient Cu-catalyzed 1,2-difunctionalization of various N-heteroarenes was developed with ether and alkyl halide at ambient temperature. This transformation involves the combination of oxidative coupling by Cu/TBHP and reduction process by 1,8-diazabicyclo[5.4.0]undec-7-ene. This method provides an efficient method to prepare various substituted dihydroazaarene derivatives via a free-radical process.

References

Feb 19, 2002·Chemical Reviews·Chryssostomos ChatgilialogluIlhyong Ryu
Jan 11, 2003·Natural Product Reports·Joseph P Michael
Aug 8, 2007·Bioorganic & Medicinal Chemistry Letters·Hidenori TakahashiDavid Thomson
Jul 12, 2008·Accounts of Chemical Research·Jared C LewisJonathan A Ellman
Jan 6, 2010·Journal of Medicinal Chemistry·Jean FotieKarl A Werbovetz
Sep 22, 2011·Journal of the American Chemical Society·Qing-An ChenYong-Gui Zhou
Jan 14, 2012·Journal of the American Chemical Society·Qing-An ChenYong-Gui Zhou
Feb 18, 2012·Journal of the American Chemical Society·Esther BoessMartin Klussmann
Feb 1, 2013·Angewandte Chemie·Andrey P Antonchick, Lars Burgmann
Aug 16, 2013·Journal of the American Chemical Society·Yongbing Liu, Haifeng Du
Oct 14, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Johannes TauberTill Opatz
Jun 18, 2015·Angewandte Chemie·Masaki NakajimaMagnus Rueping
Oct 16, 2015·Organic & Biomolecular Chemistry·Jiayu ChenLei Liu
Oct 23, 2015·Chemical Communications : Chem Comm·Amit Kumar Chattopadhyay, Stephen Hanessian
Dec 15, 2015·Chemical Communications : Chem Comm·Shekaraiah Devari, Bhahwal Ali Shah
Jan 7, 2017·Chemical Science·J Patrick LutzAbigail G Doyle
Feb 7, 2017·Angewandte Chemie·Sehoon Park, Sukbok Chang
Apr 19, 2017·Angewandte Chemie·Zhi-Yun LiuXiao-Chen Wang
Jan 19, 2018·The Journal of Organic Chemistry·Duanyang KongJiaxin Zhang
Dec 4, 1998·Angewandte Chemie·Leijun HaoHee-Gweon Woo

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