Abstract
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.
Highlights
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described
HX additions are an important class of reactions that allow the interconversion of alkenes into synthetically useful intermediates.[5]
This addition reaction shows a divergence in regioselectivity from an ionic pathway that affords the Markovnikov addition product to a free radical pathway that gives rise to the anti-Markovnikov addition product
Summary
Miranda − Molecular Sciences Department, Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC), 38206 La Laguna, Tenerife, Islas Canarias, Spain; orcid.org/0000-0002-. Cruz − “Síntesis Orgánica Sostenible, Unidad Asociada al CSIC”, Departamento de Química Orgánica, Instituto Universitario de Bio-Orgánica “Antonio González” (CIBICAN), Universidad de La Laguna, 38206 La Laguna, Tenerife, Islas Canarias, Spain. Victoria Sinka − Molecular Sciences Department, Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC), 38206 La Laguna, Tenerife, Islas Canarias, Spain. Pedro de Armas − Molecular Sciences Department, Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC), 38206 La Laguna, Tenerife, Islas Canarias, Spain. Martín − “Síntesis Orgánica Sostenible, Unidad Asociada al CSIC”, Departamento de Química Orgánica, Instituto Universitario de Bio-Orgánica “Antonio González” (CIBICAN), Universidad de La Laguna, 38206 La Laguna, Tenerife, Islas Canarias, Spain; orcid.org/0000-00030300-9636.
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