Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides

Journal of the American Chemical Society
Alexander R O VenningErik J Alexanian

Abstract

A catalytic C-H alkylation using unactivated alkyl halides and a variety of arenes and heteroarenes is described. This ring-forming process is successful with a variety of unactivated primary and secondary alkyl halides, including those with β-hydrogens. In contrast to standard polar or radical cyclizations of aromatic systems, electronic activation of the substrate is not required. The mild, catalytic reaction conditions are highly functional group tolerant and facilitate access to a diverse range of synthetically and medicinally important carbocyclic and heterocyclic systems.

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Citations

Jan 12, 2016·The Journal of Organic Chemistry·Hua WangXin-Hua Duan
May 15, 2015·Journal of the American Chemical Society·Xueqiang WangRuben Martin
Aug 10, 2016·Organic Letters·Caitlin M McMahonErik J Alexanian
Aug 30, 2016·The Journal of Organic Chemistry·Sho InagakiTomikazu Kawano
May 6, 2017·The Journal of Organic Chemistry·Jinhua ZhengJiajia Cheng
Jan 30, 2016·Angewandte Chemie·Zhixiong RuanLutz Ackermann
Apr 13, 2018·Angewandte Chemie·Zhiwei JiaoJianrong Steve Zhou
Apr 1, 2016·Chemical Communications : Chem Comm·Ran DingTeck-Peng Loh
Jan 5, 2016·Chemical Communications : Chem Comm·Jin-Tao Yu, Changduo Pan
Jul 16, 2019·Chemical Communications : Chem Comm·Sahra St John-Campbell, James A Bull
Feb 2, 2018·Organic & Biomolecular Chemistry·Wesley J OlivierAlex C Bissember
Dec 20, 2018·Chemical Communications : Chem Comm·Yang-Jie MaoDan-Qian Xu
Apr 29, 2016·Chemistry : a European Journal·Susana CastroFélix Rodríguez
Oct 16, 2015·Angewandte Chemie·Armido Studer, Dennis P Curran
Oct 21, 2020·Nature Communications·Daeun KimSoon Hyeok Hong
Feb 5, 2021·ACS Infectious Diseases·Ahmed AbdelhameedKarl A Werbovetz
Aug 14, 2019·Tetrahedron·Quentin D Tercenio, Erik J Alexanian
Aug 2, 2017·Journal of the American Chemical Society·Alexander R O VenningErik J Alexanian
Nov 18, 2018·The Journal of Organic Chemistry·Ting Li, Ping Yang
Jan 6, 2018·Journal of the American Chemical Society·Matthew R PorterJoseph J Topczewski

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