Journal ArticleDOI
Organic chemistry: Shape control in reactions with light.
Kazimer L. Skubi,Tehshik P. Yoon +1 more
TLDR
The authors show that a chiral iridium complex can serve as a sensitizer for photoredox catalysis and at the same time provide effective asymmetric induction for the enantioselective alkylation of 2-acyl imidazoles.Abstract:
The report of a light-activated catalyst that dictates the three-dimensional shape — the stereochemistry — of molecules formed in an organic reaction suggests a new strategy for controlling such reactions using visible light. See Letter p.100
The growing demand for optically active compounds in the chemical and pharmaceutical industries is focusing attention on asymmetric photocatalysis as a potentially economical means of synthesis, combining visible light photoredox chemistry with asymmetric catalysis. In this manuscript, the authors show that a chiral iridium complex can serve as a sensitizer for photoredox catalysis and at the same time provide effective asymmetric induction for the enantioselective alkylation of 2-acyl imidazoles. This new asymmetric photoredox catalyst, in which the metal centre serves simultaneously as the exclusive source of chirality, the catalytically active Lewis acid centre, and the photoredox centre, offers new opportunities for the 'green' synthesis of non-racemic chiral molecules.read more
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Journal ArticleDOI
Photomediated controlled radical polymerization
Xiangcheng Pan,Mehmet Atilla Tasdelen,Joachim Laun,Thomas Junkers,Thomas Junkers,Yusuf Yagci,Yusuf Yagci,Krzysztof Matyjaszewski +7 more
TL;DR: A comprehensive overview of the fundamentals and applications of various photomediated CRP techniques, including atom transfer radical polymerization, reversible addition-fragmentation chain transfer (RAFT), nitroxide mediated polymerization (NMP), and other procedures are discussed in this article.
Journal ArticleDOI
Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters.
TL;DR: The visible-light-driven, phase-transfer-catalyzed, enantioselective perfluoroalkylation and trifluoromethylation of cyclic β-ketoesters is described.
Journal ArticleDOI
Molecular Structural Design of Conjugated Microporous Poly(Benzooxadiazole) Networks for Enhanced Photocatalytic Activity with Visible Light
TL;DR: The valence and conduction band positions of the polymer networks can be fine-tuned by altering the substitution positions on the centered phenyl unit to match the required redox potential of the catalytic reactions under visible light.
Journal ArticleDOI
Enantioselective Organocatalytic Alkylation of Aldehydes and Enals Driven by the Direct Photoexcitation of Enamines
TL;DR: Mechanistic investigations reveal the previously hidden ability of transiently generated enamines to directly reach an electronically excited state upon light absorption while successively triggering the formation of reactive radical species from the organic halides.
Journal ArticleDOI
Metal-Free Thiocyanation of Imidazoheterocycles through Visible Light Photoredox Catalysis
TL;DR: A visible light mediated, metal-free process for the thiocyanation of imidazoheterocycles has been developed using eosin Y as a photoredox catalyst under ambient air at room temperature.
References
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Journal ArticleDOI
Solar Synthesis: Prospects in Visible Light Photocatalysis
TL;DR: A variety of reaction types have now been shown to be amenable to visible light photocatalysis via photoinduced electron transfer to or from the transition metal chromophore, as well as energy-transfer processes.
Journal ArticleDOI
Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes
TL;DR: The enantioselective intermolecular α-alkylation of aldehydes has been accomplished using an interwoven activation pathway that combines both the photoredox catalyst Ru(bpy)3Cl2 and an imidazolidinone organocatalyst.
Journal ArticleDOI
Asymmetric photoredox transition-metal catalysis activated by visible light
Haohua Huo,Xiaodong Shen,Chuanyong Wang,Lilu Zhang,Philipp Röse,Liang-An Chen,Klaus Harms,Michael Marsch,Gerhard Hilt,Eric Meggers +9 more
TL;DR: It is shown that a chiral iridium complex can serve as a sensitizer for photoredox catalysis and at the same time provide very effective asymmetric induction for the enantioselective alkylation of 2-acyl imidazoles.
Journal ArticleDOI
A Dual-Catalysis Approach to Enantioselective [2 + 2] Photocycloadditions Using Visible Light
TL;DR: A strategy for eliminating the racemic background reaction in asymmetric [2 + 2] photocycloadditions of α,β-unsaturated ketones to the corresponding cyclobutanes is described by using a dual-catalyst system consisting of a visible light–absorbing transition-metal photocatalyst and a stereocontrolling Lewis acid cocatalyst.