A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes

Nature Communications
Muliang ZhangChengjian Zhu

Abstract

The construction of an aryl ketone structural unit by means of catalytic carbon-carbon coupling reactions represents the state-of-the-art in organic chemistry. Herein we achieved the direct deoxygenative ketone synthesis in aqueous solution from readily available aromatic carboxylic acids and alkenes, affording structurally diverse ketones in moderate to good yields. Visible-light photoredox catalysis enables the direct deoxygenation of acids as acyl sources with triphenylphosphine and represents a distinct perspective on activation. The synthetic robustness is supported by the late-stage modification of several pharmaceutical compounds and complex molecules. This ketone synthetic strategy is further applied to the synthesis of the drug zolpidem in three steps with 50% total yield and a concise construction of cyclophane-braced 18-20 membered macrocycloketones. It represents not only the advancement for the streamlined synthesis of aromatic ketones from feedstock chemicals, but also a photoredox radical activation mode beyond the redox potential of carboxylic acids.

References

Sep 8, 2005·Journal of the American Chemical Society·David A SpiegelJohn L Wood
Aug 5, 2006·Science·Lukas J GoossenLaura M Levy
Jun 24, 2010·Nature Chemistry·Vijay ChudasamaStephen Caddick
Jul 28, 2011·Chemical Society Reviews·Nuria Rodríguez, Lukas J Goossen
Aug 11, 2012·The Journal of Organic Chemistry·A Stephen K HashmiMatthias Rudolph
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Jun 22, 2013·Nature Chemistry·Karl D Collins, Frank Glorius
Feb 5, 2014·Journal of the American Chemical Society·Hanchu HuangYiyun Chen
Sep 4, 2015·Angewandte Chemie·Zhe DongGuangbin Dong
Sep 26, 2015·Angewandte Chemie·Giulia BergonziniCarl-Johan Wallentin
Oct 21, 2015·Bioorganic & Medicinal Chemistry·Ai-Ying GuanMing-An Wang
Jan 26, 2016·Angewandte Chemie·Liana HieNeil K Garg
Dec 22, 2016·Journal of the American Chemical Society·Taoufik Ben HalimaStephen G Newman
Mar 8, 2017·Chemical Reviews·Ye WeiWeiping Su
Mar 25, 2017·Nature Chemistry·Haining WangChao-Jun Li
May 31, 2017·Journal of the American Chemical Society·Aristidis VasilopoulosShannon S Stahl
Jul 8, 2017·Chemical Society Reviews·Ryosuke TakiseJunichiro Yamaguchi
Jul 15, 2017·Journal of the American Chemical Society·James A WalkerLevi M Stanley
Aug 7, 2017·Journal of the American Chemical Society·Xiaheng Zhang, David W C MacMillan
Sep 21, 2017·Angewandte Chemie·Satobhisha MukherjeeFrank Glorius
Nov 28, 2017·Chemical Society Reviews·Weipeng LiChengjian Zhu
Jan 24, 2018·Accounts of Chemical Research·Pan XuChengjian Zhu
Feb 16, 2018·Angewandte Chemie·Nengneng ZhouChengjian Zhu

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Citations

Oct 24, 2018·Angewandte Chemie·Muliang ZhangJin Xie
Jan 10, 2019·Chemistry : a European Journal·Jia-Bin HanXiang-Ying Tang
Apr 18, 2019·Angewandte Chemie·Zhen LeiMing-Yu Ngai
May 3, 2019·Angewandte Chemie·Yong Xia, Armido Studer
Aug 24, 2019·Chemistry : a European Journal·Rehanguli RuziChengjian Zhu
Oct 8, 2019·Chemical Communications : Chem Comm·Pei FanChuan Wang
May 31, 2019·Chemical Communications : Chem Comm·Youngsuk KimEunsung Lee
Oct 22, 2020·Angewandte Chemie·Yusuke MasudaMasahiro Murakami
Dec 23, 2020·Chemical Society Reviews·Rolando CannalireMariateresa Giustiniano
Jul 1, 2020·IScience·Xiao-Qiang HuYang Gao
Jun 2, 2021·The Journal of Organic Chemistry·Kay MerkensAdrián Gómez-Suárez
Jun 1, 2021·ACS Central Science·Changmin XieOhyun Kwon
Jun 12, 2021·Chemical Communications : Chem Comm·Yi-Lin LiuWen-Ting Wei
Jun 18, 2021·Chemical Communications : Chem Comm·Linwei ZengSunliang Cui
Jun 25, 2021·Chemical Science·Nian LiChengjian Zhu
Jun 8, 2021·Angewandte Chemie·Anna V BayKarl A Scheidt
Aug 12, 2021·The Journal of Organic Chemistry·Muzi LiJin Xie
Sep 26, 2019·Organic Letters·John M Lopp, Valerie A Schmidt
Aug 15, 2020·The Journal of Organic Chemistry·Lan ZhengHua Yang
Sep 10, 2020·ACS Catalysis·James A Rossi-AshtonRichard J K Taylor
Jun 30, 2019·The Journal of Organic Chemistry·Shaista SultanBhahwal Ali Shah
Dec 20, 2019·The Journal of Organic Chemistry·Heng LuAo Zhang

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Methods Mentioned

BETA
hydroacylation

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