Synthesis of Chlorotrifluoromethylated Pyrrolidines by Electrocatalytic Radical Ene-Yne Cyclization

Chemistry : a European Journal
Ke-Yin YeSong Lin

Abstract

The stereoselective synthesis of chlorotrifluoromethylated pyrrolidines was achieved using anodically coupled electrolysis, an electrochemical process that combines two parallel oxidative events in a convergent and productive manner. The bench-stable and commercially available solids CF3 SO2 Na and MgCl2 were used as the functional group sources to generate CF3. and Cl. , respectively, via electrochemical oxidation, and the subsequent reaction of these radicals with the 1,6-enyne substrate was controlled with an earth-abundant Mn catalyst. In particular, the introduction of a chelating ligand allowed for the ene-yne cyclization to take place with high stereochemical control over the geometry of the alkene group in the pyrrolidine product.

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Citations

Oct 5, 2018·Chemistry : a European Journal·Wolfgang JudDavid Cantillo
Jan 27, 2019·ChemSusChem·He-Huan XuHai-Chao Xu
Sep 24, 2019·Chemical Communications : Chem Comm·Siyu TianJianbin Chen
May 28, 2020·Chemical Society Reviews·Parthasarathy GandeepanLutz Ackermann
Feb 6, 2020·Chemical Communications : Chem Comm·Tian-Jun HeJing-Mei Huang
Mar 4, 2021·Organic & Biomolecular Chemistry·Marcos R ScheideAntonio L Braga
Mar 5, 2021·Organic Letters·Jinfeng HuangZhigang Yang
Apr 27, 2021·Organic Letters·Ming DongXiaofeng Tong
Jun 2, 2021·Chemical Society Reviews·Luiz F T NovaesSong Lin
Jun 22, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Camila M KisukuriSiegfried R Waldvogel
Sep 10, 2019·Journal of the American Chemical Society·Niankai FuSong Lin
Nov 25, 2020·Journal of the American Chemical Society·Wen Zhang, Song Lin
Nov 12, 2020·The Journal of Organic Chemistry·Shaoqun ZhuHong Hou
Jan 15, 2019·Journal of the American Chemical Society·Youai QiuLutz Ackermann
Feb 23, 2020·Accounts of Chemical Research·Juno C SiuSong Lin
Nov 12, 2021·Chemical Communications : Chem Comm·James HarnedyLouis C Morrill

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