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

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

doi:10.1016/j.tetlet.2023.154432

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

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

Chemical Sciences

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2 Citations (Scopus)

Abstract

A study on the effects of ligand steric bulk in the Pd-catalysed borylation of ortho-substituted aryl bromides and chlorides under mild conditions (25 – 80 °C) is described. Catalysts derived from the less hindered biaryl phobane[3.3.1] 1 (cone angle = 178.5°) have demonstrated high efficiency for borylation of a wide array of ortho-substituted aryl bromides. Dialkylbiaryl phosphine 5 (cone angle = 181.3°) and biaryl phosphacycle 2 (cone angle = 220.0°) exhibited suitable ligand steric bulk for facile Pd-catalysed borylation of ortho-substituted aryl chlorides.

Original language	English
Article number	154432
Journal	Tetrahedron Letters
Volume	120
DOIs	https://doi.org/10.1016/j.tetlet.2023.154432
Publication status	Published - 28 Apr 2023

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Efficient system for facile access to ortho-substituted aryl boronates through palladium-catalysed borylation",

abstract = "A study on the effects of ligand steric bulk in the Pd-catalysed borylation of ortho-substituted aryl bromides and chlorides under mild conditions (25 – 80 °C) is described. Catalysts derived from the less hindered biaryl phobane[3.3.1] 1 (cone angle = 178.5°) have demonstrated high efficiency for borylation of a wide array of ortho-substituted aryl bromides. Dialkylbiaryl phosphine 5 (cone angle = 181.3°) and biaryl phosphacycle 2 (cone angle = 220.0°) exhibited suitable ligand steric bulk for facile Pd-catalysed borylation of ortho-substituted aryl chlorides.",

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AU - Lamola, Jairus L.

AU - Moshapo, Paseka T.

AU - Holzapfel, Cedric W.

AU - Makhubela, Banothile C.E.

AU - Christopher Maumela, Munaka

PY - 2023/4/28

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N2 - A study on the effects of ligand steric bulk in the Pd-catalysed borylation of ortho-substituted aryl bromides and chlorides under mild conditions (25 – 80 °C) is described. Catalysts derived from the less hindered biaryl phobane[3.3.1] 1 (cone angle = 178.5°) have demonstrated high efficiency for borylation of a wide array of ortho-substituted aryl bromides. Dialkylbiaryl phosphine 5 (cone angle = 181.3°) and biaryl phosphacycle 2 (cone angle = 220.0°) exhibited suitable ligand steric bulk for facile Pd-catalysed borylation of ortho-substituted aryl chlorides.

AB - A study on the effects of ligand steric bulk in the Pd-catalysed borylation of ortho-substituted aryl bromides and chlorides under mild conditions (25 – 80 °C) is described. Catalysts derived from the less hindered biaryl phobane[3.3.1] 1 (cone angle = 178.5°) have demonstrated high efficiency for borylation of a wide array of ortho-substituted aryl bromides. Dialkylbiaryl phosphine 5 (cone angle = 181.3°) and biaryl phosphacycle 2 (cone angle = 220.0°) exhibited suitable ligand steric bulk for facile Pd-catalysed borylation of ortho-substituted aryl chlorides.

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

Abstract

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