Journal
ACS CATALYSIS
Volume 10, Issue 15, Pages 8042-8048Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02321
Keywords
chiral alcohols; enantioselective oxidation; enantioconvergent catalysis; hypervalent iodine; photochemistry
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Funding
- DFG (Deutsche Forschungsgemeinschaft) [955/3-1]
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The application of a triazole-substituted chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes is reported. This method allows the rapid synthesis of chiral benzyl alcohols in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C-H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It initiates the radical bromination in its oxidized state through an in-situ-formed bromoiodane and in the second, Cu-catalyzed step, it acts as a chiral ligand. This work demonstrates the ability of a chiral aryl iodide catalyst acting both as an oxidant and as a chiral ligand in a highly enantioselective C-H-activating transformation. Furthermore, this concept presents an enantioconvergent hydroxylation with high selectivity using a synthetic catalyst.
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