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X-PHOS: Properties and Applications as Catalyst

Oct 23,2024

Description

X-PHOS is a phosphine ligand derived from biphenyl. Its palladium complexes exhibit high activity for Buchwald-Hartwig amination reactions involving aryl chlorides and aryl tosylates.

X-PHOS

Properties

X-PHOS is characterized by its remarkable stability and reactivity, emerges as a crucial ligand in catalytic applications, particularly in palladium-catalyzed borylation reactions.

Applications as Catalyst

as a Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.1

Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd. Synthesis of regioregular polythiophenes.

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

Application of X-PHOS in Palladium-Catalyzed Borylation Reactions

X-PHOS, a phosphine ligand, has shown significant promise in enhancing the efficiency of palladium-catalyzed Miyaura borylation reactions, a critical method for producing aryl boronic acids and esters, essential intermediates in the synthesis of active pharmaceutical ingredients (APIs). This paper demonstrates how using X-PHOS in such reactions enables significant improvements under milder conditions and with lower catalyst loadings. Typically, palladium catalysts require precise ligand control to achieve high activity and selectivity; X-PHOS offers this by providing a robust framework that stabilizes the palladium center, thus facilitating the activation of aryl halides. The advantage of using X-PHOS in the borylation process is evident in the ability to operate at lower temperatures (around 35°C) and complete reactions in less than two hours with a minimal palladium loading of 0.5 mol%. These improvements are not only cost-effective but also reduce the environmental impact associated with metal catalysts. 2, 3

References:

[1] PETER D. JOHNSON V H R Jeong Hun Sohn. Synthesis of C-15 Vindoline Analogues by Palladium-Catalyzed Cross-Coupling Reactions[J]. Journal of Organic Chemistry, 2006, 71 20: 7499-7930. DOI:10.1021/jo061243y.

[2] SANTIAGO BARROSO. Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study[J]. Journal of Organic Chemistry, 2020, 86 1: 1-1310. DOI:10.1021/acs.joc.0c01758.

[3] IRINI ABDIAJ*, JESUS ALCáZAR*. End-to-End Automated Synthesis of C(sp3)-Enriched Drug-like Molecules via Negishi Coupling and Novel, Automated Liquid–Liquid Extraction[J]. Journal of Medicinal Chemistry, 2022, 66 1: 1-1082. DOI:10.1021/acs.jmedchem.2c01646.

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    X-PHOS was first used at the beginning of the 21st century for the general amination and amidation of arenesulfonates and aryl halides and it has been used in the Pd catalyzed borylation of aryl and heteroaryl chlorides very popularly.

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X-PHOS

564483-18-7

X-PHOS manufacturers

  • X-PHOS
  • 564483-18-7 X-PHOS
  • $79.00/ kg
  • 2025-01-03
  • CAS:564483-18-7
  • Min. Order: 1kg
  • Purity: 99%
  • Supply Ability: 20ton