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Radical Cyclization of Alkene‐Tethered Ketones Initiated by Hydrogen‐Atom Transfer
Author(s) -
Saladrigas Mar,
Bosch Caroline,
Saborit Gisela V.,
Bonjoch Josep,
Bradshaw Ben
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709659
Subject(s) - alkene , chemistry , hydrogen atom , steric effects , selectivity , ring (chemistry) , hydrogen bond , radical cyclization , photochemistry , catalysis , medicinal chemistry , stereochemistry , molecule , organic chemistry , group (periodic table)
An unprecedented C−C coupling reaction between alkenes and ketones by hydrogen‐atom transfer, using Fe(acac) 3 and PhSiH 3 in EtOH, is described. This mild protocol features high site selectivity and allows the construction of sterically congested structures containing tertiary alcohols and quaternary centers. The overall process introduces a novel strategic bond disconnection for ring‐closing reactions.