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An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode

preprint
submitted on 09.04.2020 and posted on 10.04.2020 by Ayham Abazid, Nils Clamor, Boris Nachtsheim
In this article we describe an enantioselective hydroxylation of benzylic C-H bonds with a unique activation mechanism. A chiral aryl iodide catalyst initially acts as precursor for a brominating reagent which subsequently brominates the benzylic C-H bond in a non-stereoselective fashion through a radical bromination. In the second step of this transofrmation, the same catalyst acts as a chiral ligand in a Cu-catalyzed enantioconvergent substitution. We present a broad substrate scope and an intial mechanistic proposal based on a plethora of control experiments.

Funding

DFG NA955/3-1

History

Email Address of Submitting Author

nachtsheim@uni-bremen.de

Institution

University of Bremen

Country

Germany

ORCID For Submitting Author

orcid.org/0000-0002-3759-2770

Declaration of Conflict of Interest

no conflict of interest

Version Notes

first draft

Exports