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0 202603015

DOI: https://doi.org/10.6023/cjoc202603015

ARTICLE

Base-Promoted Defluorinative [3+3] Annulation: Modular Access to 6-Fluoro-1,4-dihydropyrimidines

  • Li Yanqi ,
  • Pi Chao ,
  • Gao Ning ,
  • Wu Yangjie ,
  • Cui Xiuling
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  • aHenan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, State Key Laboratory of Coking Coal Resources Green Exploitation, Pingyuan Laboratory and College of Chemistry, Zhengzhou University, Zhengzhou 450052

Received date: 2026-03-11

  Revised date: 2026-05-22

  Online published: 2026-07-24

Supported by

Natural Science Foundation of Henan (No. 252300423136), the Ministry of Science and Technology of China (No. 2016YFE0132600).

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Abstract

Herein, we reported a defluorinative [3+3] annulation between N-Phenyl arylformamidines and β-trifluoromethyl-1,3-enynes, enabling direct access to structurally diversified 6-fluoro-1,4-dihydropyrimidines (DHPs) up to 94% yields for 36 examples under transition-metal-free conditions. This protocol features broad substrate generality, excellent regioselectivity, and high atom economy. Mechanistic studies and related literature support sequence base-promoted deprotonation, nucleophilic addition/in situ nucleophilic substitution, selective C-F bond cleavage, and an intramolecular SNV cyclization. The scalability and broad potential for late-stage functionalization of the products further attest to the synthetic value of this protocol.

Key words： β-CF3-1; 3-enynes; [3+3] annulation; α; γ-dual selective defluorination; 6-fluoro-1; 4-dihydropyrimidines

Cite this article

Li Yanqi , Pi Chao , Gao Ning , Wu Yangjie , Cui Xiuling . Base-Promoted Defluorinative [3+3] Annulation: Modular Access to 6-Fluoro-1,4-dihydropyrimidines[J]. Chinese Journal of Organic Chemistry, 0 : 202603015 . DOI: 10.6023/cjoc202603015

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