Synthesis of aryl ketones or ketimines by palladium-catalyzed arene C-H addition to nitriles

The Journal of Organic Chemistry
Chengxiang Zhou, Richard C Larock

Abstract

The unprecedented palladium-catalyzed C-H addition of arenes to nitriles provides moderate to excellent yields of aryl ketones or the corresponding hindered imines. The addition of a small amount of DMSO increases the yields dramatically. Both intermolecular and intramolecular reactions are successful, although the intramolecular reactions tend to be more sluggish. This novel chemistry is believed to involve palladium-catalyzed C-H activation of the arene by electrophilic aromatic substitution, followed by the unusual carbopalladation of a nitrile. Similar reactions have been successfully developed employing arylboronic acids and nitriles. A concise route to xanthones starting from cheap starting materials has been developed employing this synthetic protocol.

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Citations

Aug 21, 2013·Accounts of Chemical Research·Daniel Solé, Israel Fernández
Jan 29, 2010·Journal of the American Chemical Society·Guohua HouFrancis Gosselin
Oct 26, 2012·The Journal of Organic Chemistry·Daniel SoléMiguel A Sierra
Feb 9, 2013·The Journal of Organic Chemistry·Guo-Ying ZhangJiang Cheng
Aug 1, 2013·The Journal of Organic Chemistry·Daniel Solé, Francesco Mariani
Aug 10, 2012·Organic Letters·Krishnamoorthy MuralirajanChien-Hong Cheng
Jan 21, 2010·Chemical Communications : Chem Comm·Chang-Liang SunZhang-Jie Shi
Jul 20, 2011·Chemical Communications : Chem Comm·Tao Miao, Guan-Wu Wang
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Feng-Ke YangKe Xu
Mar 8, 2016·The Journal of Organic Chemistry·Hongxiang WuZhuo Zeng
Oct 26, 2016·The Journal of Organic Chemistry·Moumita JashChinmay Chowdhury
Jul 8, 2017·The Journal of Organic Chemistry·Yan YanQingfeng Liu
Jul 26, 2017·Organic Letters·Jonas RydfjordMats Larhed
May 4, 2016·Chemical Communications : Chem Comm·Wenlong YuYuhong Zhang
May 9, 2015·Chemical Society Reviews·Gellért SiposReto Dorta
Oct 21, 2015·Angewandte Chemie·Christian A MalapitChris H Senanayake
Aug 10, 2018·Organic & Biomolecular Chemistry·Yesu AddepalliYun He
Aug 19, 2007·Angewandte Chemie·Daniel Solé, Olga Serrano
Jul 16, 2013·Organic & Biomolecular Chemistry·Guobing YanMinghua Yang
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Shulei PanDushen Chen
Sep 12, 2015·Angewandte Chemie·Bingwei ZhouCongyang Wang
Jan 31, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Julin GongJiuxi Chen

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