Synthesis of (Z)-Alkene-Containing Linear Conjugated Dienyl Homoallylic Alcohols by a Palladium-Catalyzed Three-Component Reaction

Horino, Yoshikazu; Sakamoto, Juri; Murakami, Miki; Sugata, Miki

doi:10.1055/s-0040-1707468

Cited by 3 publications

(2 citation statements)

References 8 publications

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“…Additionally, vinylstannanes could undergo this three‐component reaction to afford the ( Z )‐alkene‐containing linear conjugated dienyl homoallylic alcohols (Scheme 21). [43] …”

Section: Palladium‐catalyzed Nucleophilic Allylation Of Aldehydesmentioning

confidence: 99%

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Horino

Korenaga

2021

The Chemical Record

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π-Allylpalladium complexes can not only serve as electrophilic allylating agents for a broad range of nucleophiles, but also nucleophilic allylating agents for electrophiles depending on their electronic environments. In contrast to these typical reactivities of π-allylpalladium complexes, silylated and borylated π-allylpalladium species show unique reactivities that can allow versatile transformations in addition to simple allylation. Herein, four different types of transformations that are in principle achieved via the inherently reactive silylated and borylated π-allylpalladium species as common intermediates are described. An appropriate selection of ligands of the silylated and borylated π-allylpalladium species can allow control over the reaction pathways.

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“…Additionally, vinylstannanes could undergo this three‐component reaction to afford the ( Z )‐alkene‐containing linear conjugated dienyl homoallylic alcohols (Scheme 21). [43] …”

Section: Palladium‐catalyzed Nucleophilic Allylation Of Aldehydesmentioning

confidence: 99%

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Horino

Korenaga

2021

The Chemical Record

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“…Recently, we demonstrated the advantages of borylated π‐allylpalladium species I in multiple C−C‐bond‐forming reactions (Scheme 1a). For instance, species I can afford ( Z )‐homoallylic alcohols with high diastereoselectivity via the allylation of aldehydes, followed by coupling of the resulting cis ‐vinylpalladium species with organometallic reagents such as triorganoboranes, [5a] arylstannanes, [5b] and vinylstannanes [5c] (Scheme 1a, top). These encouraging results led us to extend this method to the synthesis of ( Z )‐conjugated enynyl homoallylic alcohols toward the exploration of efficient synthetic strategies.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Diastereoselective Synthesis of (Z)‐Conjugated Enynyl Homoallylic Alcohols

et al. 2021

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The diastereoselective synthesis of antihomoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described. This reaction features a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. In this reaction, Pd(0) functions as a catalyst in two fundamental steps of the tandem sequence: 1) the generation of a borylated π-allylpalladium species from bifunctional conjunctive reagents, inducing umpolung allylation of aldehydes, and 2) C(sp 2 )À C-(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility.

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N-Heterocyclic Carbene–Nickel-Catalyzed Regioselective Diarylation of Aliphatic-1,3-Dienes

et al. 2021

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Aliphatic-1,3-dienes represent a problematic class of substrates for catalytic 1,2-dicarbofunctionalization due to inherent complications of undesired allylic rearrangement, consequently giving rise to inseparable isomeric product mixtures. Here, we show that aliphatic-1,3-dienes can participate in highly efficient and site-selective 1,2-diarylation, by merging with an aryl triflate and arylmetal reagent in the presence of a sizeable N-heterocyclic carbene (NHC)−Ni(0) catalyst. Adducts containing tertiary or quaternary centers and those derived from multifunctional bioactive molecules could be obtained.

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Synthesis of (Z)-Alkene-Containing Linear Conjugated Dienyl Homoallylic Alcohols by a Palladium-Catalyzed Three-Component Reaction

Cited by 3 publications

References 8 publications

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Palladium‐Catalyzed Diastereoselective Synthesis of (Z)‐Conjugated Enynyl Homoallylic Alcohols

N-Heterocyclic Carbene–Nickel-Catalyzed Regioselective Diarylation of Aliphatic-1,3-Dienes

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