Palladium-catalyzed Csp(2)-H carbonylation of aromatic oximes: selective access to benzo[d][1,2]oxazin-1-ones and 3-methyleneisoindolin-1-ones

Chemical Communications : Chem Comm
Yanli XuHuanfeng Jiang

Abstract

A highly selective palladium-catalyzed carbonylation of Csp(2)-H bonds with aromatic oximes for the synthesis of benzo[d][1,2]oxazin-1-ones and 3-methyleneisoindolin-1-ones has been developed. Interestingly, we found that the N-OH group of the oximes could be used as a directing group and/or an internal oxidant under different conditions. This transformation is supposed to proceed through a hydroxyl-directed ortho-Csp(2)-H carbonylation or activation of vinyl Csp(2)-H bond/ortho-Csp(2)-H carbonylation process. The uses of readily available starting materials, atmospheric pressure of carbon monoxide, as well as operational simplicity make this practical and atom-economical method particularly attractive.

References

Nov 28, 2001·The Journal of Organic Chemistry·C HoarauP Grandclaudon
Dec 25, 2003·Proceedings of the National Academy of Sciences of the United States of America·Heike SchäckeKhusru Asadullah
Jun 19, 2004·The Journal of Organic Chemistry·Anne MoreauPierre Grandclaudon
Nov 4, 2004·Journal of the American Chemical Society·Kazuhiko OritoMasao Tokuda
Feb 9, 2008·Journal of the American Chemical Society·Rachel H MundayStephen L Buchwald
Oct 7, 2008·Journal of the American Chemical Society·Ramesh Giri, Jin-Quan Yu
Dec 23, 2008·Journal of the American Chemical Society·Zheng-Hui GuanXumu Zhang
Jan 27, 2009·Angewandte Chemie·Chris E HouldenKevin I Booker-Milburn
May 12, 2009·Angewandte Chemie·Anne BrennführerMatthias Beller
Mar 2, 2010·Journal of the American Chemical Society·Yichen Tan, John F Hartwig
Oct 12, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Hu LiZhang-Jie Shi
Nov 17, 2010·Chemical Communications : Chem Comm·Blanca LópezJaume Granell
Nov 19, 2010·Journal of the American Chemical Society·Eun Jeong YooJin-Quan Yu
May 6, 2011·Journal of the American Chemical Society·Nao HasegawaNaoto Chatani
Sep 14, 2011·Organic Letters·Joe W WrigglesworthKevin I Booker-Milburn
Oct 18, 2011·Chemical Communications : Chem Comm·Huoji ChenHuanfeng Jiang
Sep 18, 2012·The Journal of Organic Chemistry·Christoph KornhaaßLutz Ackermann
Oct 9, 2012·Chemical Reviews·Xiao-Feng WuMatthias Beller
Oct 12, 2012·Journal of the American Chemical Society·Zheng-Hui GuanZhi-Hui Ren
Feb 27, 2013·Journal of the American Chemical Society·Ye Wei, Naohiko Yoshikai
Mar 29, 2013·Chemical Communications : Chem Comm·Ravi Kiran ChinnagollaMasilamani Jeganmohan
Aug 31, 2013·Journal of the American Chemical Society·Wan Pyo HongShannon S Stahl
Apr 10, 2014·Accounts of Chemical Research·Shuhei SuminoIlhyong Ryu
May 31, 2014·Chemical Communications : Chem Comm·Wei DuZheng-Hui Guan
Oct 17, 2014·Chemical Communications : Chem Comm·Xiaodong TangHuanfeng Jiang
Oct 30, 2014·The Journal of Organic Chemistry·Fanghua JiHuanfeng Jiang
Nov 25, 2014·Chemical Society Reviews·Huawen HuangHuanfeng Jiang

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Citations

Jan 23, 2016·The Journal of Organic Chemistry·Zhongzhi ZhuHuanfeng Jiang
Jan 5, 2016·Organic & Biomolecular Chemistry·Huawen HuangGuo-Jun Deng
Aug 20, 2015·The Journal of Organic Chemistry·Huanfeng JiangWanqing Wu
Mar 13, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Sandip T GadgeBhalchandra M Bhanage
Oct 26, 2016·Chemical Communications : Chem Comm·Zeqiang XieQiang Zhu
Jun 13, 2017·Chemical Communications : Chem Comm·Lijun LuAiwen Lei
May 1, 2019·Chemical Communications : Chem Comm·Akira Haito, Naoto Chatani
Jul 31, 2019·Organic & Biomolecular Chemistry·Jing-Wen ZhangDan-Yun Chen
Oct 31, 2020·Chemistry : a European Journal·Risto Savela, Carolina Méndez-Gálvez
Jul 4, 2020·The Journal of Organic Chemistry·Gianluigi AlbanoLaura Antonella Aronica
Aug 5, 2021·Photochemistry and Photobiology·Kosala Thenna-HewaAnna D Gudmundsdottir

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