Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer

Mar Saladrigas; Caroline Bosch; Gisela V Saborit; Josep Bonjoch; Ben Bradshaw

doi:10.1002/anie.201709659

Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer

Angew Chem Int Ed Engl. 2018 Jan 2;57(1):182-186. doi: 10.1002/anie.201709659. Epub 2017 Dec 4.

Authors

Mar Saladrigas¹, Caroline Bosch¹, Gisela V Saborit¹, Josep Bonjoch¹, Ben Bradshaw¹

Affiliation

¹ Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-, Barcelona, Spain.

PMID: 29115722
DOI: 10.1002/anie.201709659

Abstract

An unprecedented C-C coupling reaction between alkenes and ketones by hydrogen-atom transfer, using Fe(acac)₃ and PhSiH₃ 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.

Keywords: alkenes; cyclizations; iron; ketones; radicals.

Publication types

Research Support, Non-U.S. Gov't