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Formal Alkylation of Allenes through Highly Selective Radical Cyclizations of Allene‐enes
Author(s) -
Zeng Rong,
Fu Chunling,
Ma Shengming
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107747
Subject(s) - allene , chemistry , alkene , moiety , cyclopentanes , radical cyclization , radical , photochemistry , medicinal chemistry , organic chemistry , catalysis
Something radical : The first example of alkene‐to‐allene radical cyclization of allene‐enes is reported. The highly chemoselective intermolecular radical addition reaction of the alkene and subsequent, exclusive exo ‐radical addition to the allene was realized with perfluoroalkyl radicals (see scheme). A subsequent TBAF‐promoted dehydroiodination of the cyclization products forms cyclopentanes and regenerates an allene moiety (TBAF=tetra‐ n ‐butylammonium fluoride).