Palladium/Light Induced Radical Alkenylation and Allylation of Alkyl Iodides Using Alkenyl and Allylic Sulfones

Sumino, Shuhei; Uno, Misae; Huang, Hsin-Ju; Wu, Yen‐Ku; Ryu, Ilhyong

doi:10.1021/acs.orglett.7b04050

Cited by 55 publications

(25 citation statements)

References 79 publications

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“…Allylsulfones are established trapping reagents that react with C‐radicals through addition–fragmentation to the corresponding allylated products . For example, the allylation of alkyl iodides with allylsulfones was described by Zard and Ryu . Decarboxylative and deaminative allylation were reported by Li and Liu .…”

Section: Methodsmentioning

confidence: 99%

Diversity‐Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

Xia

Studer

2019

Angew Chem Int Ed

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The diversity‐oriented desulfonylative functionalization of alkyl allyl sulfones with various sulfone‐type reagents by radical chemistry has been developed. The readily installed allylsulfonyl moiety acts as a C‐radical precursor, which is substituted by various functionalities using sulfur‐based radical trapping reagents. The generality of this approach is documented by the successful desulfonylative alkynylation, azidation, trifluoromethylthiolation, sulfenylation, trifluoromethylselenylation, halogenation, and deuteration. The method is compatible with a wide range of functional groups. Considering the deuteration, products are obtained in good yields with a high level of deuterium incorporation.

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Section: Methodsmentioning

confidence: 99%

Diversity‐Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

Xia

Studer

2019

Angew Chem Int Ed

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Section: Methodsmentioning

confidence: 99%

Diversity‐Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

Xia

Studer

2019

Angewandte Chemie

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The diversity-oriented desulfonylative functionalization of alkylallyl sulfones with various sulfone-type reagents by radical chemistry has been developed. The readily installed allylsulfonyl moiety acts as aC -radical precursor,w hich is substituted by various functionalities using sulfur-based radical trapping reagents.T he generality of this approach is documented by the successful desulfonylative alkynylation, azidation, trifluoromethylthiolation, sulfenylation, trifluoromethylselenylation, halogenation, and deuteration. The method is compatible with aw ide range of functional groups.C onsidering the deuteration, products are obtained in good yields with ahigh level of deuterium incorporation. Scheme 1. Diversity-oriented transformation by radical reactions.

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“…Ryu and co‐workers recently disclosed a light mediated photocatalytic allylation reaction using alkyl iodides by irradiation under high energy xenon or black light [61] . In 2020, Q. Wang and his group reported an improved visible light approach for allylation reactions between unactivated alkyl iodides and allyl sulfones (Scheme 21).…”

Section: Reactions Involving Atom‐transfer Processmentioning

confidence: 99%

Visible‐Light‐Induced Manganese‐Catalyzed Reactions: Present Approach and Future Prospects

2021

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Visible‐light‐induced reactions have allowed researchers to attain unorthodox bond formation and elusive chemical processes under mild and inherently safe reaction conditions. However, these methods have relied heavily on Ru‐ and Ir‐based complexes or metal‐free chromophores. While the heavy transition metal complexes are limited by their high cost, toxicity, and adverse environmental effects. Metal‐free photo‐redox catalysts are restricted due to their poorer photo‐stability. In order to overcome these shortcomings, extensive research aimed towards utilizing 3d‐transition metals has come to the forefront. Manganese, in this regard, holds great promise as a versatile and economically sustainable 3d‐transition metal catalyst. Hence, it is not surprising that recent years have witnessed several advances in visible‐light‐mediated manganese catalysis in areas of organic, polymer, and materials chemistry. Manganese‐based heterogeneous systems have also been utilized to effect dimerization and oxygenation reactions showcasing the versatility of manganese. Moreover, manganese has enabled late‐stage functionalization of valuable medicinal compounds and natural products, which are all important from the viewpoint of medicinal and pharmaceutical chemistry. In the present review, comprehensive discussions on the advances, significance, approaches, and mechanistic aspects have been added for each photochemical reaction process. Further, the reaction scope, limitations, and future prospects of visible‐light‐induced manganese catalysis have also been reviewed.

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Palladium/Light Induced Radical Alkenylation and Allylation of Alkyl Iodides Using Alkenyl and Allylic Sulfones

Cited by 55 publications

References 79 publications

Diversity‐Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

Diversity‐Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

Diversity‐Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

Visible‐Light‐Induced Manganese‐Catalyzed Reactions: Present Approach and Future Prospects

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