Merging Visible‐Light Photocatalysis and Palladium Catalysis for C−H Acylation of Azo‐ and Azoxybenzenes with α‐Keto Acids

Xu, Ning; Li, Pinhua; Xie, Zuguang; Wang, Lei

doi:10.1002/chem.201504530

Cited by 109 publications

(42 citation statements)

References 89 publications

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“…119 In addition, Wang and co-workers revealed that aryl ketones can be generated by combining photoredox-mediated acyl radical generation with directed Pd-catalyzed C–H activation. 120 …”

Section: Metallaphotoredox Catalysis: C–c Bond Formationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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In recent years, photoredox catalysis has come to the forefront in organic chemistry as a powerful strategy for the activation of small molecules. In a general sense, these approaches rely on the ability of metal complexes and organic dyes to convert visible light into chemical energy by engaging in single-electron transfer with organic substrates, thereby generating reactive intermediates. In this Perspective, we highlight the unique ability of photoredox catalysis to expedite the development of completely new reaction mechanisms, with particular emphasis placed on multicatalytic strategies that enable the construction of challenging carbon–carbon and carbon–heteroatom bonds.

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“…119 In addition, Wang and co-workers revealed that aryl ketones can be generated by combining photoredox-mediated acyl radical generation with directed Pd-catalyzed C–H activation. 120 …”

Section: Metallaphotoredox Catalysis: C–c Bond Formationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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“…The method exhibited a broad substrate scope and good functional group tolerance, and an array of ortho ‐substituted acylacetanilides were prepared in high yields under mild conditions. Subsequently, the same group described another decarboxylative ortho ‐acylation of azo‐ and azoxybenzenes 127 by using a combination of palladium catalysis and visible‐light photoredox catalysis in the presence of organic catalyst 129 at room temperature under 1.5 W of blue LED irradiation (Scheme b) …”

Section: Formation Of C−c Bondsmentioning

confidence: 99%

Visible‐Light Photoredox Decarboxylative Couplings

Jin

2017

Asian J Org Chem

187

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Carboxylica cids and their derivatives are abundant and inexpensive organic and biomass-derived platform molecules,a nd their conversion into high-value products represents an important goal. Recently,v isible-light photoredox decarboxylative couplingr eactions have become an important chemical transformation because of their wide sub-strate scope, mild reaction conditions, high efficiency,a nd practicability.T his review summarizes recenta dvances in visible-light photoredox decarboxylative coupling strategies, which include the formation of CÀCa nd CÀY( Y= heteroatom) bonds.Scheme1.Visible-lightp hotoredox decarboxylative Michael additiono fN-(acyloxy)phthalimides (LED = light-emitting diode).Scheme3.Visible-lightp hotoredox synthesis of unnatural chiral amino acids (CFL = compact fluorescent light).

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“…The azoor azoxy-benzenes could also engage in the aryl C−H acylation by dual catalysis with 9-mesityl-10-methylacridinium (Mes-AcrPh) as the photocatalyst, and the presence of O 2 · − was detected by EPR analysis (Scheme 7b). 24 …”

Section: Decarboxylative Functionalizationmentioning

confidence: 97%

Radical Decarboxylative Functionalizations Enabled by Dual Photoredox Catalysis

2016

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Organic carboxylates are readily available feedstock chemicals, and the carboxylate group is a latent activating group which can be easily removed by decarboxylation. The radical decarboxylative functionalization by photoredox catalysis undergoes rapid development recently, with which many difficult transformations can be achieved by dual photoredox catalysis. We summarize radical decarboxylative functionalizations via additional transition metal catalysts, thiol catalysts, or hypervalent iodine catalysts, which either activate the carboxylates or enable new radical transformations.

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Merging Visible‐Light Photocatalysis and Palladium Catalysis for C−H Acylation of Azo‐ and Azoxybenzenes with α‐Keto Acids

Cited by 109 publications

References 89 publications

Photoredox Catalysis in Organic Chemistry

Photoredox Catalysis in Organic Chemistry

Visible‐Light Photoredox Decarboxylative Couplings

Radical Decarboxylative Functionalizations Enabled by Dual Photoredox Catalysis

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