Building Block to Introduce Various Functional Groups

Ethyl bromodifluoroacetate (1) is a versatile building block that can introduce various functional groups depending on the reaction type. For example, 1 reacts with styrene under photoredox conditions and gives a product in which both bromo and 2-ethoxy-1,1-difluoro-2-oxoethyl groups are added to the olefin moiety.¹⁾ 1 can also introduce the 2-ethoxy-1,1-difluoro-2-oxoethyl group,²⁾ an ethyl group and a difluoromethyl group³⁾ by adjusting substances and conditions. In addition, 1 can be used as a formylating agent to introduce a formyl group to amino groups with high yields.⁴⁾ Since 1 can be used in the construction of heterocyclic rings,⁵⁾ it can be regarded as a versatile building block for introducing desired functional groups.

References

• 1) From Styrenes to Fluorinated Benzyl Bromides: A Photoinduced Difunctionalization via Atom Transfer Radical Addition
  • A. Granados, R. K. Dhungana, M. Sharique, J. Majhi, G. A. Molander, Org. Lett. 2022, 24, 4750.
• 2) Ruthenium(II)-Catalyzed meta C−H Mono- and Difluoromethylations by Phosphine/Carboxylate Cooperation
  • Z. Ruan, S.-K. Zhang, C. Zhu, P. N. Ruth, D. Stalke, L. Ackermann, Angew. Chem. Int. Ed. 2017, 56, 2045.
• 3) Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
  • A. Polley, G. Bairy, P. Das, R. Jana, Adv. Synth. Catal. 2018, 360, 4161.
• 4) Halodifluoroacetates as formylation reagents for various amines via unprecedented quadruple cleavage
  • X. Ma, S. Denga, Q. Song, Org. Chem. Front. 2018, 5, 3505.
• 5) Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors
  • F. Wang, R. Fu, J. Chen, J. Rong, E. Wang, J. Zhang, Z. Zhang, Y. Jiang, Chem. Commun. 2022, 58, 3477.

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