Abstract
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.
Highlights
Photocatalytic radical additions to imines using alkyl carboxylic acids developed by Weng and Lu and Mariano and Wang
Alemán recently reported the direct difluoromethylation of imine moieties (Scheme 6)zinc general was predicated on the single-electron oxidation of readily available difluoromethane sulfinate (DFMS) in the presence of an organophotoredox catalyst (Rhodamine 6G)
The development of new methodologies to perform the α-functionalization of imine building blocks has proven to be a subject of intense research during the past decade, as numerous approaches blocks has proven to be versatility a subject ofhave intense research during theofpast decade, as numerous approaches featuring outstanding surfaced in the context visible light photoredox catalysis
Summary
2 1 Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, Department of Organic Chemistry, Universidad Autónoma de Madrid, Madrid 28049, Spain; Madrid, Spain
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