Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Journal of the American Chemical Society
Jacob A KautzkyDavid W C MacMillan

Abstract

Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.

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Citations

Jan 30, 2019·Angewandte Chemie·Haidong LiuChao Feng
Mar 23, 2019·Chemical Communications : Chem Comm·Euan B McLeanAi-Lan Lee
Aug 15, 2019·Expert Opinion on Drug Discovery·Michael MoirMichael Kassiou
Oct 11, 2019·Beilstein Journal of Organic Chemistry·Xiaowei LiDayong Shi
May 28, 2020·Chemical Society Reviews·Li-Jie Cheng, Neal P Mankad
Jul 18, 2020·Angewandte Chemie·Alexander LippGary A Molander
Feb 6, 2020·Nature Chemistry·Barry M TrostChao-I Joey Hung
Feb 29, 2020·Chemical Science·Ana G Herraiz, Marcos G Suero
Jun 16, 2018·Chemistry : a European Journal·Matthew PaethWei Liu
Oct 17, 2018·Organic & Biomolecular Chemistry·Xiaocong ZhouYuanbin She
May 3, 2019·Science·Asik HossainOliver Reiser
Mar 24, 2020·Nature Chemistry·Patrick J SarverDavid W C MacMillan
Dec 23, 2020·Chemical Society Reviews·Rolando CannalireMariateresa Giustiniano
Aug 26, 2020·Chemistry : a European Journal·Thomas R PuleoJeffrey S Bandar
Jan 15, 2021·Organic Letters·Jiachen HeSilas P Cook
Aug 14, 2020·Chemical Reviews·Stefano Crespi, Maurizio Fagnoni
Apr 24, 2021·Chemical Society Reviews·Haiwen XiaoChaozhong Li
May 25, 2021·Chemical Society Reviews·Pan XiaoSamuel Couve-Bonnaire
Sep 17, 2019·The Journal of Organic Chemistry·Zahra Bazyar, Mona Hosseini-Sarvari
Sep 25, 2018·Journal of the American Chemical Society·Shuo GuoSilas P Cook
Oct 30, 2018·Organic Letters·Pei ZhangChaozhong Li
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Jul 10, 2019·Journal of the American Chemical Society·Xiaojun ZengWei Liu
Jul 10, 2019·Journal of the American Chemical Society·Haiwen XiaoChaozhong Li
Jul 31, 2021·Angewandte Chemie·Daniele MazzarellaTimothy Noël
Oct 27, 2018·Journal of the American Chemical Society·Pin XiaoWalter Thiel
Nov 19, 2021·Chemical Reviews·Amy Y ChanDavid W C MacMillan

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