Direct phosphonation of quinoxalin-2(1H)-ones under transition-metal-free conditions

Chemical Communications : Chem Comm
Ming GaoXiuling Cui

Abstract

A direct C-H bond phosphonation of quinoxalin-2(1H)-ones with H-phosphonates, H-phosphinates or H-phosphine oxides has been developed. A wide variety of heteroaryl phosphonates were obtained in up to 92% yield for 20 examples under transition-metal-free conditions. This protocol tolerates a broad scope of substrates and features practicality, high efficiency, environmental friendliness and atom economy.

References

Feb 8, 2002·Journal of Medicinal Chemistry·Masaaki SawaHirosato Kondo
May 24, 2003·The Journal of Organic Chemistry·Derek Van Allen, D Venkataraman
Apr 22, 2004·Journal of the American Chemical Society·Li-Biao HanShigeru Shimada
Aug 4, 2004·The Journal of Organic Chemistry·Osamu TayamaYasutaka Ishii
Jan 27, 2006·Organic Letters·Takashi KagayamaYasutaka Ishii
Feb 23, 2008·Journal of the American Chemical Society·Rebecca F RoushChristopher T Walsh
May 26, 2009·Journal of the American Chemical Society·Yuxing GaoLi-Biao Han
Feb 24, 2010·Chemical Communications : Chem Comm·Xiang-Qiang PanWei Zhang
May 27, 2011·Organic Letters·Eric L DealJean-Luc Montchamp
Jul 2, 2011·Chemical Communications : Chem Comm·Magnus RuepingRené M Koenigs
Jul 13, 2011·Organic Letters·Durga Prasad Hari, Burkhard König
Mar 17, 2012·Organic & Biomolecular Chemistry·Chaoren ShenWanbin Zhang
Apr 3, 2012·Organic Letters·Stephan M RummeltJeroen A van Bokhoven
Apr 21, 2012·Chemical Communications : Chem Comm·Chaodong HouFuwei Li
Aug 21, 2012·The Journal of Organic Chemistry·Chang-Bing XiangZhi-Zhen Huang
Nov 9, 2012·Organic & Biomolecular Chemistry·Hong-Yu ZhangShang-Dong Yang
Jun 13, 2013·Journal of the American Chemical Society·Chen-Guo FengJin-Quan Yu
Jul 25, 2013·Angewandte Chemie·Changkun LiMasahiro Murakami
Sep 24, 2013·Organic Letters·Bin YangShang-Dong Yang
Oct 29, 2013·Journal of the American Chemical Society·Yun-Rong Chen, Wei-Liang Duan
Apr 1, 2015·Organic Letters·Liping ZhuRui Wang

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Citations

Mar 28, 2017·Organic & Biomolecular Chemistry·Ming-Tao ChenQun-Li Luo
Mar 28, 2018·Organic & Biomolecular Chemistry·Ladawan SumunneeSirilata Yotphan
Jun 4, 2019·Organic & Biomolecular Chemistry·Qiumin KeXiangmei Wu
Aug 14, 2020·Organic & Biomolecular Chemistry·Hangcheng NiFei Zhao
Oct 19, 2017·Organic & Biomolecular Chemistry·Xiaobao ZengYuefei Hu
Jun 27, 2019·Organic & Biomolecular Chemistry·Wenxuan XueYulai Hu
Jun 4, 2021·Organic & Biomolecular Chemistry·Vishal Suresh KudaleJeh-Jeng Wang
Aug 13, 2021·The Journal of Organic Chemistry·Lixiao ZhaoYangjie Wu
May 30, 2019·The Journal of Organic Chemistry·Wei ZhangJin-Pei Cheng
Apr 29, 2020·Organic Letters·Zhongnan XuZhixiong Ruan
Jul 2, 2019·Organic Letters·Suman PalIsabelle Gillaizeau
Nov 3, 2021·Organic & Biomolecular Chemistry·Sha PengLuo Yang
Dec 3, 2021·Organic & Biomolecular Chemistry·Yi-Na LiZhen Wang

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