Citation: Quanbin Jiang, Hui Jiao, Long Jiang, Xiaodan Zhao. A catalytic thiolation/dethiolation strategy for the ring-opening of cyclopropenes to access α,β-unsaturated nitriles and carbonyl compounds[J]. Chinese Chemical Letters, ;2026, 37(11): 112354. doi: 10.1016/j.cclet.2025.112354 shu

A catalytic thiolation/dethiolation strategy for the ring-opening of cyclopropenes to access α,β-unsaturated nitriles and carbonyl compounds

Quanbin Jiang ^a ,
Hui Jiao ^a ,
Long Jiang ^b ,
Xiaodan Zhao ^{a, *,}

a.
Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, IGCME, Sun Yat-sen University, Guangzhou 510006, China
b.
Instrument Analysis & Research Center, Sun Yat-sen University, Guangzhou 510275, China

zhaoxd3@mail.sysu.edu.cn

Received Date: 18 August 2025
Revised Date: 22 December 2025
Accepted Date: 31 December 2025
Available Online: 31 December 2025

Figures(5)

An efficient catalytic thiolation/dethiolation strategy for the ring-opening transformation of cyclopropenes is reported. The reaction occurs via the formation of a vinylogous Pummerer intermediate followed by a dethiolation Pummerer fragmentation step. A wide range of valuable products including α,β-unsaturated nitriles and carbonyl compounds can be efficiently synthesized in these reactions. The resultant products are readily transformed into other valuable molecules. The hydrogenation experiment supports the generation of the vinylogous thionium ion as a crucial intermediate in this transformation.
- Cyclopropenes,
- Alkenyl nitriles,
- Pummerer intermediate,
- Electrophilic thiolation,
- Synthetic methods
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