（來源：康龍化成）

轉(zhuǎn)自：康龍化成

Transformation of α,β-Unsaturated Aldehydes with a Small Amount of Electricity: Cyanosilylation, Isomerization, and Nucleophilic Addition

Mayu Fujii, Nanaho Ueno, Koichi Mitsudo, Eisuke Sato,* and Seiji Suga*

Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University, Okayama, Japan

—Org. Lett., 2025, DOI: 10.1021/acs.orglett.5c01790

Recommended by Yuquan Liu_PT

KEY WORDS:Electro chemistry, catalytic electrolysis, cyanosilylation, Isomerization, Nucleophilic Addition(反應(yīng)類型), α,β-Unsaturated Aldehydes (原料), carboxylic acid derivatives (產(chǎn)物), C(sp2)-O, C(sp2)-S, C(sp2)-N, (成鍵類型), electron-catalyzed (其他)

ABSTRACT: An electrochemical method was developed to convert α,β-unsaturated aldehydes into carboxylic acid derivatives via cyanosilylation, isomerization, and nucleophilic addition. This reaction is more sustainable than the usual electrochemical organic reaction because this reaction proceeds catalytically with active species generated by a very small amount of electricity. Furthermore, scale-up synthesis with a flow reactor has been achieved.

Previous Work and This Work

Proposed Mechanism

Substrate scope

Scale-up Synthesis in the Batch and Flow Process

Prof. Eisuke Sato and Seiji Sugaet al have developed an electrochemical transformation of α,β-unsaturated aldehydes to carboxylic acid derivatives. This reaction sequence proceeds by a series of cyanosilylation, isomerization, andnucleophilic addition. The results of several control experiments indicate that the driving force of the reaction sequence could be the electro-generated base.