Citation: Qiuyun Li, Yannan Zhu, Yining Wang, Gang Qi, Wen-Juan Hao, Kelu Yan, Bo Jiang. Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones[J]. Chinese Chemical Letters, ;2024, 35(9): 109494. doi: 10.1016/j.cclet.2024.109494 shu

Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones

Qiuyun Li ^{a, *,} ,
Yannan Zhu ^a ,
Yining Wang ^a ,
Gang Qi ^a ,
Wen-Juan Hao ^b ,
Kelu Yan ^{c, *,} ,
Bo Jiang ^{b, *,}

a.
School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051, China
b.
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, China
c.
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China

^☆

^th

liqiuyun@ycit.edu.cn

yankl@qfnu.edu.cn

jiangchem@jsnu.edu.cn

Received Date: 29 September 2023
Revised Date: 21 December 2023
Accepted Date: 2 January 2024
Available Online: 6 January 2024

Figures(5)

Catalytic C-H activation-initiated annulation reactions have emerged as a versatile strategy for the efficient construction of diverse ring structural units and complex cyclic molecules in synthetic chemistry. Herein, we describe a new Rh(Ⅲ)-catalyzed C-H activation-initiated transdiannulation reaction of N, N-dimethyl enaminones with gem-difluorocyclopropenes in the presence of H₂O, enabling a facile and oxygen transfer access to ring-fluorinated tricyclic γ-lactones with a 6-5 ring-junction tetrasubstituted stereocenter. This approach features bond-forming/annulation efficiency, good functional group tolerance and complete regioselectivity, which may include a complex process consisting of Rh(Ⅲ)-catalyzed C(sp²)H activation, cyclic alkene insertion, defluorinated ring-opening of gem-difluorocyclopropane, intramolecular oxygen transfer, intramolecular cyclization and oxidative hydration.
- C-H bond activation,
- Enaminones,
- Transannulation,
- Oxygen transfer,
- Regioselectivity
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