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Palladium‐Initiated Radical Cascade Stereoselective Iodofluoroalkylation/Cycloisomerization of Ene‐vinylidenecyclopropanes
Author(s) -
Yang Song,
Xu Qin,
Shi Min
Publication year - 2016
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.201601625
Subject(s) - cycloisomerization , stereoselectivity , palladium , chemistry , iodide , atom economy , cascade , catalysis , ene reaction , radical cyclization , alkyl , medicinal chemistry , organic chemistry , chromatography
A novel and convenient palladium‐initiated radical cascade stereoselective iodofluoroalkylation/cycloisomerization of ene‐vinylidenecyclopropanes with fluoroalkyl iodides has been developed. The reaction proceeds under mild reaction conditions with high atom economy and stereoselectivity, thereby allowing an efficient access to a variety of difluoromethylated or perfluoroalkylated pyrrolidines tethered with an alkyl iodide. Two plausible radical pathways for the transformation have been proposed on the basis of the results of control experiments and previous reports, which in one case it was thought that palladium(0) was an initiator rather than a catalyst.