Copper-Catalyzed N-Arylation of Azoles and Mannich-Type Coupling of Ketones and Azoles under Metal-Free Conditions

The Journal of Organic Chemistry
Kai SunXin Wang

Abstract

A new process has been developed for the copper-catalyzed direct N-arylation of five-membered heterocycles with azoles. Five-membered heterocycles bearing an acetyl group also underwent a Mannich-type reaction with activated azoles to give the corresponding β-amino ketones under metal-free conditions. These reactions exhibited wide substrate scope, high functional group tolerance, and ease of operation, making them useful tools with numerous potential applications in synthetic chemistry.

References

Jan 9, 1999·Clinical Microbiology Reviews·D J SheehanC M Sibley
Dec 26, 2001·The Journal of Organic Chemistry·K OgawaS C Rasmussen
Mar 29, 2003·The Journal of Organic Chemistry·Mark W HooperJohn F Hartwig
May 12, 2005·Angewandte Chemie·Huw M L Davies, Matthew S Long
Aug 27, 2005·Organic Letters·Mark D CharlesStephen L Buchwald
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Mar 4, 2009·Organic Letters·Daiki MonguchiAtsunori Mori
Oct 29, 2009·Organic Letters·Qiu Wang, Stuart L Schreiber
Dec 31, 2009·Chemistry, an Asian Journal·Caroline J Scheuermann
Jan 22, 2011·Journal of the American Chemical Society·Kai SunQian Zhang
Oct 29, 2011·Angewandte Chemie·Alison E WendlandtShannon S Stahl
Dec 23, 2011·Chemical Society Reviews·Bei-Li LuMin Shi
Feb 18, 2012·Journal of the American Chemical Society·Esther BoessMartin Klussmann
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
Mar 6, 2012·Angewandte Chemie·Junmin ZhangYonggui Robin Chi
Aug 30, 2012·Angewandte Chemie·Shengtao Ding, Ning Jiao
Jan 10, 2013·Journal of the American Chemical Society·Maxim O Ratnikov, Michael P Doyle
Jun 13, 2013·Chemical Communications : Chem Comm·Yunhe LvQian Zhang
Oct 1, 2013·Chemical Society Reviews·Jitender Bariwal, Erik Van der Eycken
Nov 13, 2013·Chemical Society Reviews·Marie-Laure Louillat, Frederic W Patureau
Dec 12, 2013·Chemistry : a European Journal·Xue JiangJianliang Xiao
Feb 5, 2014·Organic Letters·Nagaraju MupparapuRam A Vishwakarma
Mar 13, 2014·Chemical Communications : Chem Comm·Xuxing ChenChunhao Yang
Oct 14, 2014·Organic Letters·Sichang WangYuanjiang Pan
Apr 17, 2015·The Journal of Organic Chemistry·Xiaoyan LuoWei-Ping Deng
Oct 20, 2015·Organic & Biomolecular Chemistry·Bing HaoAntony M Hooper
May 4, 1998·Angewandte Chemie·Michael ArendNikolaus Risch

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Citations

Feb 9, 2017·Chemistry, an Asian Journal·Kai SunWeimin Du
Jun 15, 2017·Organic & Biomolecular Chemistry·Kai SunXin Wang
Mar 16, 2017·Chemical Communications : Chem Comm·Chunlan SongAiwen Lei
Sep 6, 2018·Organic & Biomolecular Chemistry·Kai SunBing Zhang
Apr 4, 2019·Organic & Biomolecular Chemistry·Kai SunBing Zhang
Oct 19, 2019·Angewandte Chemie·Jin-Feng YuJin-Quan Yu
Dec 19, 2018·Advanced Synthesis & Catalysis·Magdalena R AndrzejewskaMahesh K Lakshman
Sep 4, 2019·Organic & Biomolecular Chemistry·Xin WangKai Sun
Oct 28, 2017·The Journal of Organic Chemistry·Hongbo ZhuJinmao You
Dec 25, 2019·The Journal of Organic Chemistry·Kai SunBing Zhang

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