Powerful Phosphine Ligand for the Synthesis of ortho-Tetrasubstituted Biaryls

HFTPhos is a Buchwald ligand-based biaryl phosphine that serves as an efficient catalyst ligand for Suzuki-Miyaura cross-coupling reactions.¹⁾ Owing to its electron-deficient heptafluorotolyl (HFT) group bearing multiple fluorine substituents, HFTPhos enables secondary interactions with the palladium center in the transition state, thereby significantly accelerating the reductive elimination step. As a result, highly hindered tetra-ortho-substituted biaryl compounds can be synthesized with exceptionally low catalyst loadings (as little as 0.025 mol% Pd), and the palladium catalyst achieves turnover numbers of up to 90000. The scope of this catalyst system is remarkably broad and includes applications in the synthesis of intermediates for biologically active natural products such as (-)-steganone.²⁾ Tetra-ortho-substituted biaryl moieties are attracting increasing attention as key structural elements in pharmaceuticals, agrochemicals, and advanced functional materials. Therefore HFTPhos provides a powerful tool for the efficient development of next-generation functional molecules.

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References

• 1) Highly Active Catalyst for Suzuki–Miyaura Coupling to Form Sterically Demanding Biaryls: Electronic Control of Pd through the Secondary Interaction Using a Buchwald-Type Ligand Bearing a Fluorinated Aryl Ring
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• 2) A Concise Atroposelective Formal Synthesis of (-)-Steganone
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• 3) Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling
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• 4) Third Generation Buchwald Precatalysts with XPhos and RuPhos: Multigram Scale Synthesis, Solvent-Dependent Isomerization of XPhos Pd G3 and Quality Control by ¹H- and ³¹P-NMR Spectroscopy
  • S. O. Sotnik, A. M. Mishchenko, E. B. Rusanov, A. V. Kozytskiy, K. S. Gavrilenko, S. V. Ryabukhin, D. M. Volochnyuk, S. V. Kolotilov, Molecules 2021, 26, 3507.

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