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Updated: Jun 22, 2025
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic Enantioselective Hydroxylation of Tertiary Propargylic C(sp3)-H Bonds in Acyclic Systems: a Kinetic
Min Cao1,2, Hongliang Wang1,2, Fangao Hou1
1School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China.
Abstract:
Direct site-selective and enantioselective oxyfunctionalization of C(sp3)-H bonds to form alcohols with a general scope, with predictable selectivities, and in preparatively useful yields represents a paradigm shift in the standard logic of synthetic organic chemistry. However, the knowledge of either enzymatic or nonenzymatic asymmetric hydroxylation of tertiary C-H bonds for enantioenriched tertiary alcohol synthesis is sorely lacking. Here, we report a practical manganese-catalyzed enantio-differentiating hydroxylation of tertiary propargylic C-H bonds in acyclic systems, producing a wide range of structurally diverse enantioenriched tertiary propargyl alcohols in high efficiency with extremely efficient chemo- and enantio-discrimination. Other features include the use of C-H substrates as the limiting reagent, noteworthy functional group compatibility, great synthetic utilities, and scalability. The findings serve as a blueprint for the development of metal-catalyzed asymmetric oxidation of challenging substrates.
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