Efficient system for facile access to ortho-substituted aryl boronates through palladium-catalysed borylation

Lamola, Jairus L.; Moshapo, Paseka T.; Holzapfel, Cedric W.; Makhubela, Banothile C.E.; Maumela, Munaka C.

doi:10.1016/j.tetlet.2023.154432

Tetrahedron Letters

2023

DOI: 10.1016/j.tetlet.2023.154432

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Efficient system for facile access to ortho-substituted aryl boronates through palladium-catalysed borylation

Jairus L. Lamola

Paseka T. Moshapo

Cedric W. Holzapfel

et al.

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“…Since the first report in 1995, modifications to the Miyaura borylation components, including the base, palladium/ligand catalyst, and solvent, have allowed for the development of milder borylation conditions. The borylation of aryl bromides and chlorides at room temperature is one example of improved reactivity enabled by these advances. , …”

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confidence: 99%

Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations

Klootwyk,

Ruble,

Cumming

et al. 2024

J. Org. Chem.

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The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.

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mentioning

confidence: 99%

Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations

Klootwyk,

Ruble,

Cumming

et al. 2024

J. Org. Chem.

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Recent Expedition in Pd‐ and Rh‐Catalyzed C_(Ar)−B Bond Formations and Their Applications in Modern Organic Syntheses

Choy,

Tse,

Kwong

2023

Chemistry An Asian Journal

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Transition metal‐catalyzed borylation has emerged as a powerful and versatile strategy for synthesizing organoboron compounds. These compounds have found widespread applications in various aspects, including organic synthesis, materials science, and medicinal chemistry. This review provides a concise summary of the recent advances in palladium‐ and rhodium‐catalyzed borylation from 2013 to 2023. The review covers the representative examples of catalysts, substrates scope and reaction conditions, with particular emphasis on the development of catalyst systems, such as phosphine ligands, NHC‐carbene, and more. The diverse array of borylative products obtained for further applications in Suzuki‐Miyaura coupling, and other transformations, are also discussed. Future directions in this rapidly evolving field, with the goal of designing more efficient, selective borylation methodologies are highlighted, too.

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Efficient system for facile access to ortho-substituted aryl boronates through palladium-catalysed borylation

Cited by 2 publications

References 77 publications

Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations

Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations

Recent Expedition in Pd‐ and Rh‐Catalyzed C_(Ar)−B Bond Formations and Their Applications in Modern Organic Syntheses

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Efficient system for facile access to ortho-substituted aryl boronates through palladium-catalysed borylation

Cited by 2 publications

References 77 publications

Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations

Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations

Recent Expedition in Pd‐ and Rh‐Catalyzed C(Ar)−B Bond Formations and Their Applications in Modern Organic Syntheses

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About

Recent Expedition in Pd‐ and Rh‐Catalyzed C_(Ar)−B Bond Formations and Their Applications in Modern Organic Syntheses