Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox

Journal of the American Chemical Society
Chi Chip Le, David W C MacMillan

Abstract

In this study we demonstrate that molecular fragments, which can be readily coupled via a simple, in situ RO-C═OR bond-forming reaction, can subsequently undergo metal insertion-decarboxylation-recombination to generate Csp(2)-Csp(3) bonds when subjected to metallaphotoredox catalysis. In this embodiment the conversion of a wide variety of mixed anhydrides (formed in situ from carboxylic acids and acyl chlorides) to fragment-coupled ketones is accomplished in good to high yield. A three-step synthesis of the medicinal agent edivoxetine is also described using this new decarboxylation-recombination protocol.

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Citations

Jan 29, 2016·Journal of the American Chemical Society·Xiangcheng PanKrzysztof Matyjaszewski
Feb 9, 2016·Organic Letters·Matthieu JouffroyGary A Molander
Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
Jun 28, 2016·Journal of the American Chemical Society·Lucile Anthore-DalionSamir Z Zard
Jul 2, 2016·Organic Letters·Gabrielle H Lovett, Brian A Sparling
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Apr 12, 2017·Journal of the American Chemical Society·Quanyou Feng, Rong Tong
Nov 20, 2016·Chemistry : a European Journal·Tuhin Patra, Debabrata Maiti
Feb 19, 2016·Angewandte Chemie·Candice L Joe, Abigail G Doyle
Jun 13, 2017·Organic Letters·Javad Amani, Gary A Molander
Jul 12, 2017·Organic Letters·Zhongdong SunMasakatsu Shibasaki
Apr 5, 2016·Chemical Communications : Chem Comm·Faben A CruzVy M Dong
Feb 20, 2018·Angewandte Chemie·Leyre MarzoBurkhard König
Sep 12, 2018·Chemical Communications : Chem Comm·Paul DingwallSteven V Ley
Oct 7, 2018·Angewandte Chemie·John A MilliganGary A Molander
Apr 17, 2019·Journal of Mass Spectrometry : JMS·Elettra L PiacentinoVictor Ryzhov
Sep 19, 2019·Angewandte Chemie·Eugenio GandolfoPaolo Melchiorre
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Mar 31, 2021·Journal of the American Chemical Society·Benxiang ZhangChaozhong Li
Oct 31, 2020·Journal of the American Chemical Society·Xiaomin ShuHaohua Huo
Jun 18, 2021·Chemical Communications : Chem Comm·Linwei ZengSunliang Cui
Sep 24, 2019·Organic Letters·Andrei V IosubJoakim Bergman
Oct 24, 2018·Journal of the American Chemical Society·Laura K G AckermanAbigail G Doyle
Feb 6, 2020·Journal of the American Chemical Society·Tairin KawasakiMasahiro Murakami
Nov 19, 2021·Chemical Reviews·Amy Y ChanDavid W C MacMillan

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