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Synthesis of Chlorotrifluoromethylated Pyrrolidines by Electrocatalytic Radical Ene‐Yne Cyclization
Author(s) -
Ye KeYin,
Song Zhidong,
Sauer Gregory S.,
Harenberg Johannes H.,
Fu Niankai,
Lin Song
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802167
Subject(s) - ene reaction , chemistry , pyrrolidine , electrolysis , electrochemistry , radical , electrosynthesis , stereoselectivity , catalysis , alkene , ligand (biochemistry) , combinatorial chemistry , substrate (aquarium) , functional group , medicinal chemistry , organic chemistry , electrode , electrolyte , biochemistry , oceanography , receptor , geology , polymer
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 CF 3 SO 2 Na and MgCl 2 were used as the functional group sources to generate CF 3 . 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.