Iridium‐Catalyzed Allylic Alkylations of Sodium Phenyl Selenide

Cui, Ruimin; Guo, Xinwen; Shi, Zheng; Zhao, Xiaoming

doi:10.1002/cjoc.201200836

Cited by 3 publications

(2 citation statements)

References 74 publications

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“…Selenide nucleophiles have also been applied in Ir-catalyzed allylic substitution reactions; however, linear products were typically obtained from these reactions due to rearrangement of the initially formed branched isomers to the thermodynamically more stable linear isomers. 375 Branched products were isolated from two substrates following a fast workup and reduction. Saturated branched compounds were obtained in 31−34% yields with 90−94% ee (Scheme 281).…”

Section: Selenidementioning

confidence: 99%

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

et al. 2018

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In this review, we summarize the origin and advancements of iridiumcatalyzed asymmetric allylic substitution reactions during the past two decades. Since the first report in 1997, Ir-catalyzed asymmetric allylic substitution reactions have attracted intense attention due to their exceptionally high regio-and enantioselectivities. Ircatalyzed asymmetric allylic substitution reactions have been significantly developed in recent years in many respects, including ligand development, mechanistic understanding, substrate scope, and application in the synthesis of complex functional molecules. In this review, an explicit outline of ligands, mechanism, scope of nucleophiles, and applications is presented.

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Section: Selenidementioning

confidence: 99%

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

et al. 2018

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“…In 2012, Zhao and co-workers explored an asymmetric allylation between sodium phenyl selenide and allylic carbonates with an iridium catalyst made from Feringa's ligand L4. 115 These allylations gave the linear products rather than the branched isomers (Scheme 69). The isomerization between the branched and linear isomers occurred during the reaction.…”

Section: Scheme 68mentioning

confidence: 99%

Carbon-Sulfur Bond Formation via Metal-Catalyzed Allylations of Sulfur Nucleophiles

Liu

Zhao

2013

Synthesis

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The development of practical approaches for the construction of carbon-sulfur bonds is of interest to scientists. In particular, carbon-sulfur bond formation by transition-metal-catalyzed allylations has been attracting great attention. Allylic sulfides are important substances owing to their broad applications in synthetic and pharmaceutical areas. The alkene and sulfur moieties in allylic sulfides can lead to numerous transformations. This review details the development of carbon-sulfur bond formation through palladium-catalyzed rearrangements, palladium-catalyzed allylations, iridium-catalyzed regio-and enantioselective allylations and miscellaneous metal-catalyzed allylic substitutions. Carbon-selenium bond formations via metal-catalyzed allylic substitutions are also reviewed. 1 Introduction 2 Carbon-Sulfur Bond Formation via Palladium-Catalyzed Reactions 2.1 Rearrangements of Allylic Substrates 2.2 Allylations 2.3 Asymmetric Allylations 3 Carbon-Sulfur Bond Formation via Iridium-Catalyzed Regio-and Enantioselective Allylations 4 Carbon-Sulfur Bond Formation via Miscellaneous Metal-Catalyzed Reactions 4.1 Nickel 4.2 Ruthenium 4.3 Gallium 4.4 Iron 5 Carbon-Selenium Bond Formation via Metal-Catalyzed Allylic Substitutions 6 Conclusions

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