中国化学快报(英文版)2024,Vol.35Issue(9) :145-149.DOI:10.1016/j.cclet.2024.109494

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

Qiuyun Li Yannan Zhu Yining Wang Gang Qi Wen-Juan Hao Kelu Yan Bo Jiang
中国化学快报(英文版)2024,Vol.35Issue(9) :145-149.DOI:10.1016/j.cclet.2024.109494

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

Qiuyun Li 1Yannan Zhu 1Yining Wang 1Gang Qi 1Wen-Juan Hao 2Kelu Yan 3Bo Jiang2
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作者信息

  • 1. School of Chemistry and Chemical Engineering,Yancheng Institute of Technology,Yancheng 224051,China
  • 2. School of Chemistry & Materials Science,Jiangsu Normal University,Xuzhou 221116,China
  • 3. Key Laboratory of Life-Organic Analysis of Shandong Province,School of Chemistry and Chemical Engineering,Qufu Normal University,Qufu 273165,China
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Abstract

Catalytic C-H activation-initiated annulation reactions have emerged as a versatile strategy for the effi-cient 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 oxy-gen transfer access to ring-fluorinated tricyclic γ-lactones with a 6-5 ring-junction tetrasubstituted stere-ocenter.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.

Key words

C-H bond activation/Enaminones/Transannulation/Oxygen transfer/Regioselectivity

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出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
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