Photocatalytic dehydrogenative C-C coupling of acetonitrile to succinonitrile

Xian Zhou, Xiaofeng Gao, Mingjie Liu, Zirui Gao, Xuetao Qin, Wenhao Xu, Shitong Ye, Wenhua Zhou, Haoan Fan, Jing Li, Shurui Fan, Lei Yang, Jie Fu, Dequan Xiao, Lili Lin (), Ding Ma () and Siyu Yao ()
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Xian Zhou: Zhejiang University
Xiaofeng Gao: Peking University
Mingjie Liu: Zhejiang University
Zirui Gao: Peking University
Xuetao Qin: Peking University
Wenhao Xu: Zhejiang University
Shitong Ye: Zhejiang University
Wenhua Zhou: Zhejiang University
Haoan Fan: Zhejiang University
Jing Li: Zhejiang University
Shurui Fan: Zhejiang University of Technology
Lei Yang: Zhejiang Henglan Science and Technology Co. Ltd
Jie Fu: Zhejiang University
Dequan Xiao: University of New Haven
Lili Lin: Zhejiang University of Technology
Ding Ma: Peking University
Siyu Yao: Zhejiang University

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

Abstract: Abstract The coupling of acetonitrile into succinonitrile, an important terminal dinitrile for value-added nylon production, via a dehydrogenative route is highly attractive, as it combines the valuable chemical synthesis with the production of green hydrogen energy. Here, we demonstrate that it is possible to achieve a highly selective light driven dehydrogenative coupling of acetonitrile molecules to synthesize succinonitrile using anatase TiO2 based photocatalysts in aqueous medium under mild conditions. Under optimized conditions, the formation rate of succinonitrile reaches 6.55 mmol/(gcat*h), with over 97.5% selectivity to target product. Mechanism studies reveal that water acts as cocatalyst in the reaction. The excited hole of anatase semiconductor oxidizes water forming hydroxyl radical, which subsequently assists the cleavage of sp3 C-H bond of acetonitrile to generate ·CH2CN radical for further C-C coupling. The synergy between TiO2 and Pt cocatalyst is important to enhance the succinonitrile selectivity and prevent undesirable over-oxidation and hydrolysis. This work offers an alternative route to prepare succinonitrile based on renewable energy under mild conditions and avoid the use of toxic reagents and stoichiometric oxidative radical initiators.

Date: 2022
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DOI: 10.1038/s41467-022-32137-y

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