Palladium(II)-Catalyzed, Heteroatom-Directed, Regioselective C-H Nitration of Anilines Using Pyrimidine as a Removable Directing Group

Organic Letters
Govind Goroba PawarManmohan Kapur

Abstract

A new palladium-catalyzed, heteroatom-directed strategy for C-H nitration of anilines is described. This C-H functionalization reaction is highly ortho-selective and results in very good yields. The highlight of the work is the use of pyrimidine as the removable directing group. This approach constitutes one of the rare methods of ortho-nitration of anilines, a reaction that is normally very difficult to achieve via traditional approaches.

References

Aug 24, 2000·Chemical Research in Toxicology·V Purohit, A K Basu
Jul 3, 2003·Journal of the American Chemical Society·Shlomo Rozen, Mira Carmeli
Dec 25, 2003·Angewandte Chemie·G K Surya Prakash, Markus Etzkorn
Jun 18, 2004·Organic Letters·G K Surya PrakashGeorge A Olah
Aug 29, 2006·Bioorganic & Medicinal Chemistry Letters·Jack J ChenY George Zhang
Oct 26, 2006·Journal of the American Chemical Society·Kami L HullMelanie S Sanford
Nov 2, 2006·Journal of the American Chemical Society·Stefan J PastineDalibor Sames
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Sep 10, 2009·Journal of the American Chemical Society·Brett P Fors, Stephen L Buchwald
Nov 11, 2009·Journal of the American Chemical Society·David C PowersTobias Ritter
Feb 11, 2010·Angewandte Chemie·G K Surya Prakash, Thomas Mathew
Mar 2, 2011·Organic Letters·Fuhong XiaoChao-Jun Li
Mar 2, 2011·Chemical Communications : Chem Comm·Wenhui WangJiang Cheng
Mar 3, 2011·Angewandte Chemie·Géraldine Rousseau, Bernhard Breit
Mar 23, 2011·The Journal of Organic Chemistry·Jinlei ChenXingwei Li
Apr 12, 2011·Chemistry : a European Journal·Haijun YangHua Fu
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Nov 15, 2011·Organic Letters·Lin ZhangQun Liu
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Mar 14, 2012·Organic Letters·Srimanta MannaDebabrata Maiti
Apr 14, 2012·Nature·Amanda J Hickman, Melanie S Sanford
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Dec 1, 2012·Chemical Communications : Chem Comm·Brenden KilpatrickSteve Arns
Feb 28, 2013·Organic & Biomolecular Chemistry·Guobing Yan, Minghua Yang
Aug 15, 2013·Organic Letters·Daniela Sustac Roman, André B Charette
Aug 21, 2013·The Journal of Organic Chemistry·Changduo PanChengjian Zhu

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Citations

May 18, 2016·Journal of the American Chemical Society·Zhoulong FanAo Zhang
Dec 29, 2016·The Journal of Organic Chemistry·Riki Das, Manmohan Kapur
Jun 22, 2017·The Journal of Organic Chemistry·Desaboini Nageswar RaoParthasarathi Das
Feb 10, 2018·Chemistry, an Asian Journal·Paridhi Saxena, Manmohan Kapur
Aug 9, 2017·Organic & Biomolecular Chemistry·Vinod G LandgeEkambaram Balaraman
Jul 7, 2018·Organic & Biomolecular Chemistry·Arumugavel MuruganDuddu S Sharada
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Sep 20, 2018·Organic & Biomolecular Chemistry·Motoki ItoShigeo Sugiyama
Jan 3, 2019·Organic & Biomolecular Chemistry·Virendra Kumar Tiwari, Manmohan Kapur
Jan 16, 2019·Organic & Biomolecular Chemistry·Li-Rui SongAo Zhang

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