Poster Presentation 51st Lorne Proteins Conference 2026

Copper palladium catalyzed synthesis of boryl substituted monofluoroalkenes (#201)

AYMAN M. Y. SULIMAN 1 , EbrahimAlkhalil Ahmed 2 , Gong Tian-Jun 3 , Yao Fu 3
  1. Division of Natural and Applied Sciences, Global Health Research Center, Duke Kunshan University, Kunshan, Jiangsu, China
  2. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou , Zhejiang, China
  3. School of Chemistry and Materials Science, University of Science and Technology of China, Hefei, Anhui, China

Background and aims

Fluorine-containing organic compounds are highly valued for their ability to improve stability, lipophilicity, and biological activity. Monofluoroalkenes, in particular, act as metabolically stable amide bioisosteres and are widely used as intermediates in pharmaceuticals, agrochemicals, and materials science. Despite their utility, efficient and general methods to access monofluoroalkenes with high stereochemical control remain limited. ¹ This study aimed to develop a modular and practical catalytic strategy to address this limitation.

Methods

We designed a dual copper/palladium catalytic system that integrates alkyne borylcupration with palladium-catalyzed C–C bond activation and selective C–F bond cleavage of gem-difluorocyclopropanes. ²

Results

The dual catalytic system delivered boryl-substituted monofluoroalkenes in good to high yields with excellent regio- and stereoselectivity. It showed broad substrate scope, functional group tolerance, and enabled late-stage modification of complex molecules.

Conclusion

This copper-palladium strategy offers an efficient and versatile route to monofluoroalkenes, thereby expanding synthetic options for fluorine chemistry and its applications in drug discovery.

References

  1. a) Purser S.; Moore P. R.; Swallow S.; Gouverneur V. Chem. Soc. Rev. 2008, 37, 320–330.
    b) Wang F.; Zhu N.; Chen P.; Ye J.; Liu G. Angew. Chem. Int. Ed. 2015, 54, 9356–9360.
  2. a) Xu J.; Ahmed E.-A. M. A.; Xiao B.; Lu Q.; Wang Y.; Yu C.; Fu Y.* Angew. Chem.Int. Ed., 2015, 54, 8231–8235, b) Ahmed E-A. M. A; Suliman A.; Gong T.-J.*; Fu Y.* Org. Lett., 2019, 21, 5645−5649. c) Ahmed E-A. M. A; Suliman A.; Gong T.-J.*; Fu Y.* Org. Lett., 2020, 22, 1414–1419. d) Suliman A#; Ahmed E-A. M. A#; Gong T.-J.*; Fu Y.* Org. Lett., 2021, 23, 3259−3263; e) Suliman A#; Ahmed E-A. M. A#; Gong T.-J.*; Fu Y.* Chem. Commun., 2021, 57, 6400−6403.