Carboxylative Coupling of Chloromethyl(hetero)arenes with Allyltrimethoxysilane Catalyzed by Palladium Nanoparticles

Song, Jiliang; Feng, Xiujuan; Yamamoto, Yoshinori; Almansour, Abdulrahman I.; Arumugam, Natarajan; Kumar, Raju Suresh; Bao, Ming

doi:10.1002/ajoc.201600510

Cited by 10 publications

(8 citation statements)

References 62 publications

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“…The reaction has good compatibility with methyl, methoxy, halogen (fluorine, chlorine and bromine), nitro, methoxycarbonyl and other functional groups (Scheme 19). [28] In this transformation, additive TBAF plays three roles: stabilizer of catalyst, activator of organosilicon reagent and promoter of carbonÀ carbon double bond isomerization. TEM image shows the presence of (2.69 � 0.83) nmsized palladium nanoparticles in the reaction mixture (Figure 9).…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Palladium‐Catalyzed Three‐Component Coupling Reaction via Benzylpalladium Intermediate

Zhang

Feng

Bao

2021

The Chemical Record

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Transition-metal catalyzed multi-component reactions have captured the attention of researchers in organic synthesis and drug synthesis due to their advantages of simple operation, easy availability of raw materials and without separation of intermediates. Among the multicomponent reactions, the three-component processes have been developed into effective organic procedures. This personal account reviews our and other group's studies on the development of three-component coupling reaction for the rapid construction of two new chemical bonds simultaneously via benzylpalladium intermediates. Catalyst-switched three-component reactions of benzyl halides, activated olefins, and allyltributylstannane were successfully conducted to produce the corresponding benzylallylation products. Activation and conversion of carbon monoxide and carbon dioxide via π-benzylpalladium intermediates provide access to a wide range of unsaturated ketones and esters with excellent functional group tolerance. Meanwhile, other methods to produce benzylpalladium intermediates, including Heck insertion of alkenes into arylpalladium complexes, the oxidative addition of benzyl carbonate to palladium complexes and palladiumÀ carbene migratory insertion, were also highlighted.

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Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Palladium‐Catalyzed Three‐Component Coupling Reaction via Benzylpalladium Intermediate

Zhang

Feng

Bao

2021

The Chemical Record

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“…According to the author proposed mechanism, the reaction proceeded via an oxidative addition/transmetalation/ coordination/nucleophilic addition/reductive elimination/ isomerization sequential process. 51…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Recent advances in the application of nano-catalysts for Hiyama cross-coupling reactions

et al. 2019

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“…Over the past few years, metal nanoparticles (MNPs) catalysts have attracted much interest and been widely used in many types of coupling reactions [1][2][3], such as Heck [4], Suzuki [5,6], Sonogashira [7,8], Stille [9,10], Ullmann [11,12], and Hiyama reactions [13,14]. MNPs catalysts are usually better than the corresponding molecular catalysts on catalytic activity due to their large surface area, so, they need protective agents to avoid the formation of bulk metal.…”

Section: Introductionmentioning

confidence: 99%

Effect of the types of stabilizers and size distribution on catalytic activity of palladium nanoparticles in the carboxylative coupling reaction

Sun

Gao

et al. 2018

SN Appl. Sci.

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Palladium nanoparticles (Pd NPs) generated in situ and stabilized by quaternary ammonium salts were used in threecomponent coupling reaction as the catalyst. Cations and anions of quaternary ammonium salts influenced the catalytic activity of Pd NPs, and tetrabutyl-ammonium bromide (TBAB) proved to be the best stabilizer. (2.23 ± 0.58) nm-sized Pd NPs showed the best catalytic activity under the molar ratio 1/30 [Pd(acac) 2 /TBAB]. The mercury poisoning test demonstrated the reaction occurred on the surface of Pd NPs. Pd NPs could be recycled for four times without significant loss in catalytic activity.

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Carboxylative Coupling of Chloromethyl(hetero)arenes with Allyltrimethoxysilane Catalyzed by Palladium Nanoparticles

Cited by 10 publications

References 62 publications

Palladium‐Catalyzed Three‐Component Coupling Reaction via Benzylpalladium Intermediate

Palladium‐Catalyzed Three‐Component Coupling Reaction via Benzylpalladium Intermediate

Recent advances in the application of nano-catalysts for Hiyama cross-coupling reactions

Effect of the types of stabilizers and size distribution on catalytic activity of palladium nanoparticles in the carboxylative coupling reaction

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