Organophotocatalytic radical-polar cross-coupling of styrene boronic acids and redox-active esters

Jeremy Brals; Nicholas D'Arcy-Evans; Thomas McGuire; Allan J. B. Watson

doi:10.1055/a-2179-6570

Organophotocatalytic radical-polar cross-coupling of styrene boronic acids and redox-active esters

Jeremy Brals, Nicholas D'Arcy-Evans, Thomas McGuire, Allan J. B. Watson^*

^*Corresponding author for this work

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

Abstract

We report the development of a radical-polar cross-coupling reaction using styrene boronic acids and redox-active esters under organophotoredox catalysis. The reaction proceeds through a formal polarity-mismatched radical addition. The use of an organic photocatalyst enabled very low loadings of the electron-shuttle additive and accelerated reaction times compared to established processes. The scope of the reaction is explored, and the utility of the products is demonstrated.

Original language	English
Pages (from-to)	A-D
Number of pages	4
Journal	Synlett
Volume	34
DOIs	https://doi.org/10.1055/a-2179-6570
Publication status	Published - 23 Oct 2023

Keywords

Esters
Styrylboronic acids
Photocatalysis
Radical-polar cross-coupling

Access to Document

10.1055/a-2179-6570Licence: CC BY

Brals_2023_Synlett_Organophotocatalytic_CCBY
Copyright © 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution and reproduction, so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)
Final published version, 335 KBLicence: CC BY

1 Finished
1 Active

Allan Watson Programme Grant: Boron: Beyond the Reagent
Watson, A. J. B. (PI), Morris, R. E. (CoI), Smith, A. D. (CoI) & Zysman-Colman, E. (CoI)
UK Research and Innovation
1/05/23 → 30/04/28
Project: Standard
A biochemical boron tagging stategy: A biochemical boron tagging strategy for biomolecule visualisation and profiling
Watson, A. J. B. (PI)
The Leverhulme Trust
1/09/22 → 31/08/24
Project: Fellowship

Dataset underpinning "Organophotocatalytic Radical-Polar Cross-Coupling of Styrene Boronic Acids and Redox-Active Esters"
Watson, A. J. B. (Creator), University of St Andrews, 9 Nov 2023
DOI: 10.17630/aad8f3fd-74e8-4bdd-aaab-2950f9be9ae1
Dataset

File

Cite this

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title = "Organophotocatalytic radical-polar cross-coupling of styrene boronic acids and redox-active esters",

abstract = "We report the development of a radical-polar cross-coupling reaction using styrene boronic acids and redox-active esters under organophotoredox catalysis. The reaction proceeds through a formal polarity-mismatched radical addition. The use of an organic photocatalyst enabled very low loadings of the electron-shuttle additive and accelerated reaction times compared to established processes. The scope of the reaction is explored, and the utility of the products is demonstrated.",

keywords = "Esters, Styrylboronic acids, Photocatalysis, Radical-polar cross-coupling",

author = "Jeremy Brals and Nicholas D'Arcy-Evans and Thomas McGuire and Watson, {Allan J. B.}",

note = "Funding: AstraZeneca; EPSRC - EP/W007517; Leverhulme Trust - RF-2022-014.",

year = "2023",

month = oct,

day = "23",

doi = "10.1055/a-2179-6570",

language = "English",

volume = "34",

pages = "A--D",

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TY - JOUR

T1 - Organophotocatalytic radical-polar cross-coupling of styrene boronic acids and redox-active esters

AU - Brals, Jeremy

AU - D'Arcy-Evans, Nicholas

AU - McGuire, Thomas

AU - Watson, Allan J. B.

N1 - Funding: AstraZeneca; EPSRC - EP/W007517; Leverhulme Trust - RF-2022-014.

PY - 2023/10/23

Y1 - 2023/10/23

N2 - We report the development of a radical-polar cross-coupling reaction using styrene boronic acids and redox-active esters under organophotoredox catalysis. The reaction proceeds through a formal polarity-mismatched radical addition. The use of an organic photocatalyst enabled very low loadings of the electron-shuttle additive and accelerated reaction times compared to established processes. The scope of the reaction is explored, and the utility of the products is demonstrated.

AB - We report the development of a radical-polar cross-coupling reaction using styrene boronic acids and redox-active esters under organophotoredox catalysis. The reaction proceeds through a formal polarity-mismatched radical addition. The use of an organic photocatalyst enabled very low loadings of the electron-shuttle additive and accelerated reaction times compared to established processes. The scope of the reaction is explored, and the utility of the products is demonstrated.

KW - Esters

KW - Styrylboronic acids

KW - Photocatalysis

KW - Radical-polar cross-coupling

U2 - 10.1055/a-2179-6570

DO - 10.1055/a-2179-6570

M3 - Article

SN - 0936-5214

VL - 34

SP - A-D

JO - Synlett

JF - Synlett

ER -

Organophotocatalytic radical-polar cross-coupling of styrene boronic acids and redox-active esters

Abstract

Keywords

Access to Document

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Projects

Allan Watson Programme Grant: Boron: Beyond the Reagent

A biochemical boron tagging stategy: A biochemical boron tagging strategy for biomolecule visualisation and profiling

Datasets

Dataset underpinning "Organophotocatalytic Radical-Polar Cross-Coupling of Styrene Boronic Acids and Redox-Active Esters"

Cite this