An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode
Keyword(s):
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.<br>
2009 ◽
Vol 57
(11)
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pp. 1179-1188
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2012 ◽
Vol 77
(21)
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pp. 9813-9825
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2019 ◽
Vol 587
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pp. 117241
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2008 ◽
Vol 40
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pp. 219-226
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