Electroreductive coupling of benzaldehyde by balancing the formation and dimerization of the ketyl intermediate

Jia Yu, Peng Zhang, Lulu Li, Kailang Li, Gong Zhang, Jia Liu, Tuo Wang, Zhi-Jian Zhao and Jinlong Gong ()
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Jia Yu: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Peng Zhang: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Lulu Li: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Kailang Li: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Gong Zhang: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Jia Liu: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Tuo Wang: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Zhi-Jian Zhao: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University
Jinlong Gong: Key Laboratory for Green Chemical Technology of Ministry of Education, Tianjin University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Electroreductive coupling of biomass-derived benzaldehyde offers a sustainable approach to producing value-added hydrobenzoin. The low efficiency of the reaction mainly ascribes to the mismatch of initial formation and subsequent dimerization of ketyl intermediates (Ph-CH = O → Ph-C·-OH → Ph-C(OH)-C(OH)-Ph). This paper describes a strategy to balance the active sites for the generation and dimerization of ketyl intermediates by constructing bimetallic Pd/Cu electrocatalysts with tunable surface coverage of Pd. A Faradaic efficiency of 63.2% and a hydrobenzoin production rate of up to 1.27 mmol mg−1 h−1 (0.43 mmol cm−2 h−1) are achieved at −0.40 V vs. reversible hydrogen electrode. Experimental results and theoretical calculations reveal that Pd promotes the generation of the ketyl intermediate, and Cu enhances their dimerization. Moreover, the balance between these two sites facilitates the coupling of benzaldehyde towards hydrobenzoin. This work offers a rational strategy to design efficient electrocatalysts for complex reactions through the optimization of specified active sites for different reaction steps.

Date: 2022
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DOI: 10.1038/s41467-022-35463-3

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