From Aldehyde to Ketone via Water‐Accelerated Molybdenum‐Photocatalysis

Author:

Meng Jiaolong1,Jia Yixin1,Li Chengliang1,Jiang Xuefeng123ORCID

Affiliation:

1. Hainan Institute of East China Normal University State Key Laboratory of Molecular & Process Engineering Shanghai Key Laboratory of Green Chemistry and Chemical Processes School of Chemistry and Molecular Engineering East China Normal University North Zhongshan Road 3663 Shanghai 200062 China

2. School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang Henan 453007 China

3. State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

Abstract

AbstractThe efficient “on water” protocol was developed by employing molybdenum‐based polyoxometalate [N(C4H9)4]2[Mo6O19] as the photocatalyst. This water‐accelerated photoinduced process affords versatile ketones from aldehydes straightforwardly, showcasing exceptional substrate generality. Its applicability to life‐related molecules such as amino acids, peptides, and sugars, further demonstrates its potential for bioorthogonal application. The mechanistic investigation highlights the hydrogen atom transfer (HAT) process between the excited‐state POM and benzaldehyde for acyl radical formation. This highly reactive acyl radical is readily trapped by the Michael acceptor, thereby enabling subsequent C−H functionalization. Highly efficient gram‐scale flow operation underlines the industrial applicability of this transformative strategy.

Funder

National Natural Science Foundation of China

Science and Technology Commission of Shanghai Municipality

Publisher

Wiley

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