A Clean and Selective Radical Homocoupling Employing Carboxylic Acids with Titania Photoredox Catalysis

David W. Manley; John C. Walton

doi:10.1021/ol502625w

A Clean and Selective Radical Homocoupling Employing Carboxylic Acids with Titania Photoredox Catalysis

David W. Manley, John C. Walton^*

^*Corresponding author for this work

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

57 Citations (Scopus)

5 Downloads (Pure)

Abstract

A titania photoredox catalysis protocol was developed for the homocoupling of C-centered radicals derived from carboxylic acids. Intermolecular reactions were generally efficient and selective, furnishing the desired dimers in good yields under mild neutral conditions. Selective cross-coupling with two acids proved unsuccessful. An intramolecular adaptation enabled macrocycles to be prepared, albeit in modest yields.

Original language	English
Pages (from-to)	5394-5397
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	20
Early online date	7 Oct 2014
DOIs	https://doi.org/10.1021/ol502625w
Publication status	Published - 17 Oct 2014

Keywords

Coupling-reactions
Organic-synthesis
Natural-products
Tertiary-amines
Polymerizations
Photocatalysis
Alkylations

Access to Document

10.1021/ol502625w

manley2014organiclett5394
Copyright © 2014 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 671 KB

Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis
Walton, J. C. (PI) & McBurney, R. T. (Researcher)
EPSRC
1/10/10 → 31/03/14
Project: Standard

Cite this

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title = "A Clean and Selective Radical Homocoupling Employing Carboxylic Acids with Titania Photoredox Catalysis",

abstract = "A titania photoredox catalysis protocol was developed for the homocoupling of C-centered radicals derived from carboxylic acids. Intermolecular reactions were generally efficient and selective, furnishing the desired dimers in good yields under mild neutral conditions. Selective cross-coupling with two acids proved unsuccessful. An intramolecular adaptation enabled macrocycles to be prepared, albeit in modest yields.",

keywords = "Coupling-reactions, Organic-synthesis, Natural-products, Tertiary-amines, Polymerizations, Photocatalysis, Alkylations",

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doi = "10.1021/ol502625w",

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AU - Manley, David W.

AU - Walton, John C.

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N2 - A titania photoredox catalysis protocol was developed for the homocoupling of C-centered radicals derived from carboxylic acids. Intermolecular reactions were generally efficient and selective, furnishing the desired dimers in good yields under mild neutral conditions. Selective cross-coupling with two acids proved unsuccessful. An intramolecular adaptation enabled macrocycles to be prepared, albeit in modest yields.

AB - A titania photoredox catalysis protocol was developed for the homocoupling of C-centered radicals derived from carboxylic acids. Intermolecular reactions were generally efficient and selective, furnishing the desired dimers in good yields under mild neutral conditions. Selective cross-coupling with two acids proved unsuccessful. An intramolecular adaptation enabled macrocycles to be prepared, albeit in modest yields.

KW - Coupling-reactions

KW - Organic-synthesis

KW - Natural-products

KW - Tertiary-amines

KW - Polymerizations

KW - Photocatalysis

KW - Alkylations

U2 - 10.1021/ol502625w

DO - 10.1021/ol502625w

M3 - Article

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EP - 5397

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

A Clean and Selective Radical Homocoupling Employing Carboxylic Acids with Titania Photoredox Catalysis

Abstract

Keywords

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Projects

Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis

Cite this