Open AccessIron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
Author(s) -
Daniel A. Cruz,
Victoria Sinka,
Pedro de Armas,
H. Sebastián Steingruber,
Israel Fernández,
Victor S. Martı́n,
Pedro O. Miranda,
Juan I. Padrón
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c02186
Subject(s) - markovnikov's rule , regioselectivity , chemistry , reagent , density functional theory , bromide , copper , medicinal chemistry , organic chemistry , combinatorial chemistry , computational chemistry , catalysis
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti -Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.
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