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Mechanistic Insights into Aerobic C(sp³)-H Hydroxylation: A Catalytic Reaction or Not

15 October 2025, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

The mechanism of aerobic C(sp³)-H hydroxylation to α-hydroxy ketone is investigated by multiple quantum chemical computations. An alkali metal assisted electron transfer (AET) is proposed to drive the triplet-to-singlet transition for C-O bond formation. The O-O bond cleavage is the key to catalytic conversion, which depends on different alkali metal bases and reductants.

Keywords

aerobic C(sp³)-H hydroxylation
multiple quantum chemical computations
alkali metal assisted electron transfer

Supplementary materials

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Supporting Information
Description
Electronic supplementary information (ESI) available: Text, figures, DFT calculation and DLPNO-CCSD(T) calculation details, MS-CASPT2 calculation results for MECP, additional reaction profiles and cartesian coordinates.
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Version History

Oct 15, 2025 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2025-85t3c
D O I: 10.26434/chemrxiv-2025-85t3c [opens in a new tab]

Funding

National Key Research and Development Program of China
2021YFA1500100
National Natural Science Foundation of China
92156017
National Natural Science Foundation of China
21890722
“Frontiers Science Center for New Organic Matter”, Nankai University
63181206
Haihe Laboratory of Sustainable Chemical Transformation of Tianjin
24HHWCSS00019

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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