Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Jairus L. Lamola; Paseka T. Moshapo; Cedric W. Holzapfel; Munaka Christopher Maumela

doi:10.1016/j.tetlet.2021.153572

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Jairus L. Lamola, Paseka T. Moshapo, Cedric W. Holzapfel, Munaka Christopher Maumela

Chemical Sciences

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Catalysts based on the combination of Pd(OAc)₂ and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Original language	English
Article number	153572
Journal	Tetrahedron Letters
Volume	88
DOIs	https://doi.org/10.1016/j.tetlet.2021.153572
Publication status	Published - 5 Jan 2022

Keywords

Aryl chlorides
Biaryl
Borylation
Ligands
Phosphatrioxa-adamantane
Steric

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2021.153572

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title = "Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands",

abstract = "Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).",

keywords = "Aryl chlorides, Biaryl, Borylation, Ligands, Phosphatrioxa-adamantane, Steric",

author = "Lamola, {Jairus L.} and Moshapo, {Paseka T.} and Holzapfel, {Cedric W.} and {Christopher Maumela}, Munaka",

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doi = "10.1016/j.tetlet.2021.153572",

language = "English",

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T1 - Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

AU - Lamola, Jairus L.

AU - Moshapo, Paseka T.

AU - Holzapfel, Cedric W.

AU - Christopher Maumela, Munaka

PY - 2022/1/5

Y1 - 2022/1/5

N2 - Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

AB - Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

KW - Aryl chlorides

KW - Biaryl

KW - Borylation

KW - Ligands

KW - Phosphatrioxa-adamantane

KW - Steric

UR - http://www.scopus.com/inward/record.url?scp=85120774860&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2021.153572

DO - 10.1016/j.tetlet.2021.153572

M3 - Article

AN - SCOPUS:85120774860

SN - 0040-4039

VL - 88

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153572

ER -

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Abstract

Keywords

ASJC Scopus subject areas

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