Palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of poly(pseudo)halogenated arenes

On Ying Yuen; Shan Shan Ng; Wai Hang Pang; Chau Ming So

doi:10.1016/j.jorganchem.2023.122983

Palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of poly(pseudo)halogenated arenes

On Ying Yuen, Shan Shan Ng, Wai Hang Pang, Chau Ming So

Research output: Journal article publication › Journal article › Academic research › peer-review

1 Citation (Scopus)

Abstract

This paper presents general examples of the palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of polyhalogenated aryl triflates with a reactivity order of C–Br > C–Cl > C–OTf. A diverse array of bromo(hetero)aryl triflates was successfully coupled with (hetero)aryl boronic acids, achieving excellent reactivity and chemoselectivity. This was accomplished using a catalyst system composed of Pd(OAc)₂ and SelectPhos (L1), with catalyst loadings reducible to as low as 0.02 mol% Pd. The sequential double functionalization of bromochloroaryl triflates was also demonstrated successfully, paving the way for the synthesis of terphenyl derivatives.

Original language	English
Article number	122983
Journal	Journal of Organometallic Chemistry
Volume	1005
DOIs	https://doi.org/10.1016/j.jorganchem.2023.122983
Publication status	Published - 1 Feb 2024

Keywords

Bromochloroaryl triflates
Chemoselectivity
Palladium
Phosphine ligand
Suzuki–Miyaura

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

More information

10.1016/j.jorganchem.2023.122983

Cite this

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title = "Palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of poly(pseudo)halogenated arenes",

abstract = "This paper presents general examples of the palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of polyhalogenated aryl triflates with a reactivity order of C–Br > C–Cl > C–OTf. A diverse array of bromo(hetero)aryl triflates was successfully coupled with (hetero)aryl boronic acids, achieving excellent reactivity and chemoselectivity. This was accomplished using a catalyst system composed of Pd(OAc)2 and SelectPhos (L1), with catalyst loadings reducible to as low as 0.02 mol% Pd. The sequential double functionalization of bromochloroaryl triflates was also demonstrated successfully, paving the way for the synthesis of terphenyl derivatives.",

keywords = "Bromochloroaryl triflates, Chemoselectivity, Palladium, Phosphine ligand, Suzuki–Miyaura",

author = "Yuen, {On Ying} and Ng, {Shan Shan} and Pang, {Wai Hang} and So, {Chau Ming}",

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T1 - Palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of poly(pseudo)halogenated arenes

AU - Yuen, On Ying

AU - Ng, Shan Shan

AU - Pang, Wai Hang

AU - So, Chau Ming

PY - 2024/2/1

Y1 - 2024/2/1

N2 - This paper presents general examples of the palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of polyhalogenated aryl triflates with a reactivity order of C–Br > C–Cl > C–OTf. A diverse array of bromo(hetero)aryl triflates was successfully coupled with (hetero)aryl boronic acids, achieving excellent reactivity and chemoselectivity. This was accomplished using a catalyst system composed of Pd(OAc)2 and SelectPhos (L1), with catalyst loadings reducible to as low as 0.02 mol% Pd. The sequential double functionalization of bromochloroaryl triflates was also demonstrated successfully, paving the way for the synthesis of terphenyl derivatives.

AB - This paper presents general examples of the palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of polyhalogenated aryl triflates with a reactivity order of C–Br > C–Cl > C–OTf. A diverse array of bromo(hetero)aryl triflates was successfully coupled with (hetero)aryl boronic acids, achieving excellent reactivity and chemoselectivity. This was accomplished using a catalyst system composed of Pd(OAc)2 and SelectPhos (L1), with catalyst loadings reducible to as low as 0.02 mol% Pd. The sequential double functionalization of bromochloroaryl triflates was also demonstrated successfully, paving the way for the synthesis of terphenyl derivatives.

KW - Bromochloroaryl triflates

KW - Chemoselectivity

KW - Palladium

KW - Phosphine ligand

KW - Suzuki–Miyaura

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DO - 10.1016/j.jorganchem.2023.122983

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AN - SCOPUS:85180365054

SN - 0022-328X

VL - 1005

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

M1 - 122983

ER -

Palladium-catalyzed chemoselective Suzuki–Miyaura cross-coupling reaction of poly(pseudo)halogenated arenes

Abstract

Keywords

ASJC Scopus subject areas

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