α-Functionalization of Imines via Visible Light Photoredox Catalysis

The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction...

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Main Authors: Alberto F. Garrido-Castro, M. Carmen Maestro, José Alemán
Format: Article
Language:English
Published: MDPI AG 2020-05-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/10/5/562
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author Alberto F. Garrido-Castro
M. Carmen Maestro
José Alemán
author_facet Alberto F. Garrido-Castro
M. Carmen Maestro
José Alemán
author_sort Alberto F. Garrido-Castro
collection DOAJ
description The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis.
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spelling doaj.art-dee34b23bd9c479eb059c277db9dfeb42023-11-20T00:55:28ZengMDPI AGCatalysts2073-43442020-05-0110556210.3390/catal10050562α-Functionalization of Imines via Visible Light Photoredox CatalysisAlberto F. Garrido-Castro0M. Carmen Maestro1José Alemán2Department of Organic Chemistry, Universidad Autónoma de Madrid, 28049 Madrid, SpainDepartment of Organic Chemistry, Universidad Autónoma de Madrid, 28049 Madrid, SpainDepartment of Organic Chemistry, Universidad Autónoma de Madrid, 28049 Madrid, SpainThe innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis.https://www.mdpi.com/2073-4344/10/5/562aminesiminesphotoredox catalysisradical additionsradical–radical couplingsstereoselectivity
spellingShingle Alberto F. Garrido-Castro
M. Carmen Maestro
José Alemán
α-Functionalization of Imines via Visible Light Photoredox Catalysis
Catalysts
amines
imines
photoredox catalysis
radical additions
radical–radical couplings
stereoselectivity
title α-Functionalization of Imines via Visible Light Photoredox Catalysis
title_full α-Functionalization of Imines via Visible Light Photoredox Catalysis
title_fullStr α-Functionalization of Imines via Visible Light Photoredox Catalysis
title_full_unstemmed α-Functionalization of Imines via Visible Light Photoredox Catalysis
title_short α-Functionalization of Imines via Visible Light Photoredox Catalysis
title_sort α functionalization of imines via visible light photoredox catalysis
topic amines
imines
photoredox catalysis
radical additions
radical–radical couplings
stereoselectivity
url https://www.mdpi.com/2073-4344/10/5/562
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