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Relevant academic research and scientific papers

Pd Nanoparticles Embedded Into MOF-808: Synthesis, Structural Characteristics, and Catalyst Properties for the Suzuki–Miyaura Coupling Reaction

Abstract: A heterogeneous single-site catalyst Pd@MOF-808 was successfully synthesized by water-based, green synthesis procedure. The catalytic experiments exhibited the Pd@MOF-808 promoted efficiently the Suzuki–Miyaura coupling reaction without the assistance of organic phosphine ligands at atmospheric pressure conditions. The catalyst also could be applied in the gram-scale synthesis of industrially anti-inflanmatory analgestic Fenbufen. Graphic Abstract: [Figure not available: see fulltext.]

Suzuki-miyaura cross-coupling of 1,8-diaminonaphthalene (dan)-protected arylboronic acids

We report a Suzuki-Miyaura cross-coupling reaction of 1,8-diaminonaphthalene (dan)-protected arylboronic acids in the presence of KOt-Bu, which does not require the removal of the dan moiety. Notably, the use of aryl-B(dan) in the Suzuki-Miyaura reaction provides a complementary solution to the protodeboronation problems. The base KOt-Bu plays a crucial role for the promotion of these cross-coupling reactions as it enables the formation of a borate salt. This reaction protocol was extended to the one-pot sequential Suzuki-Miyaura cross-coupling reaction of 4-[(pin)B]C6H4-B(dan), wherein the "less reactive" aryl-B(dan) moiety was cross-coupled preferentially.

LiCl-Accelerated multimetallic cross-coupling of aryl chlorides with aryl triflates

While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen.

A Highly Active Cobalt Catalyst System for Kumada Biaryl Cross-Coupling

A highly active cobalt catalyst system has been developed for the cross-coupling reactions of arylmagnesium reagents and aryl bromides. In the presence of 1 mol% CoCl 2, 2 mol% IPr·HCl and 2 mol% NaO t Bu, a wide range of (hetero)biaryls are prepared in 51-99% yields at room temperature within a short reaction time.

Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates

Using a recently discovered precatalyst, the first Pd-catalyzed Suzuki-Miyaura reactions using aryl sulfamates that occur at room temperature are reported. In complementary work, it is demonstrated that a related precatalyst can facilitate the coupling of aryl silanolates, which are less toxic and reactive nucleophiles than boronic acids with aryl chlorides. By combining our results using modern electrophiles and nucleophiles, the first Hiyama-Denmark reactions using aryl sulfamates are reported.

Highly efficient and magnetically recyclable graphene-supported Pd/Fe3O4 nanoparticle catalysts for Suzuki and Heck cross-coupling reactions

Herein, we report a facile and efficient one-step method for the synthesis of highly active, Pd/Fe3O4 nanoparticles supported on graphene nanosheets (Pd/Fe3O4/G) that exhibit excellent catalytic activity for Suzuki and Heck coupling reactions and that can be magnetically separated from the reaction mixture and recycled multiple times without loss of catalytic activity. The synthesis approach is based on the Microwave (MW)-assisted reduction of palladium and ferric nitrates in the presence of graphene oxide (GO) nanosheets using hydrazine hydrate as the reducing agent. The results provide a fundamental understanding of the system variables by comparing the catalytic activity and recyclability of four different catalysts with different properties. The most active and recyclable catalyst contains 7.6 wt% Pd nanoparticles with 4-6 nm diameters in Pd(0) oxidation state well-dispersed with 30 wt% Fe3O4 nanoparticles with 12-16 nm diameters on highly reduced GO containing a C/O ratio of 8.1. These combined properties produce remarkable catalytic activity for Suzuki cross coupling reactions under MW reaction conditions with an extremely high turnover number (TON) of 9250 and turn over frequency (TOF) of 111,000 h-1 at 80°C. The magnetic properties imparted by the Fe3O4 component of the catalyst enables the catalyst to be easily isolated and recycled, thus greatly simplifying the ability to purify the reaction products and increasing the economic value of the catalyst. The utility of these magnetic catalysts towards Suzuki and Heck cross coupling reactions with a variety of functionalized substrates was also demonstrated.

Highly efficient and magnetically recyclable graphene-supported Pd/Fe3O4 nanoparticle catalysts for Suzuki and Heck cross-coupling reactions

Herein, we report a facile and efficient one-step method for the synthesis of highly active, Pd/Fe3O4 nanoparticles supported on graphene nanosheets (Pd/Fe3O4/G) that exhibit excellent catalytic activity for Suzuki and Heck coupling reactions and that can be magnetically separated from the reaction mixture and recycled multiple times without loss of catalytic activity. The synthesis approach is based on the Microwave (MW)-assisted reduction of palladium and ferric nitrates in the presence of graphene oxide (GO) nanosheets using hydrazine hydrate as the reducing agent. The results provide a fundamental understanding of the system variables by comparing the catalytic activity and recyclability of four different catalysts with different properties. The most active and recyclable catalyst contains 7.6 wt% Pd nanoparticles with 4-6nm diameters in Pd(0) oxidation state well-dispersed with 30wt% Fe3O4 nanoparticles with 12-16 nm diameters on highly reduced GO containing a C/O ratio of 8.1. These combined properties produce remarkable catalytic activity for Suzuki cross coupling reactions under MW reaction conditions with an extremely high turnover number (TON) of 9250 and turn over frequency (TOF) of 111,000 h-1 at 80 °C. The magnetic properties imparted by the Fe3O4 component of the catalyst enables the catalyst to be easily isolated and recycled, thus greatly simplifying the ability to purify the reaction products and increasing the economic value of the catalyst. The utility of these magnetic catalysts towards Suzuki and Heck cross coupling reactions with a variety of functionalized substrates was also demonstrated.

Selective Kumada biaryl cross-coupling reaction enabled by an iron(iii) alkoxide-N-heterocyclic carbene catalyst system

A catalyst system comprising Fe2(OtBu)6 and an N-heterocyclic carbene ligand enables efficient syntheses of (hetero)biaryls from the reactions of aryl Grignard reagents with a diverse spectrum of (hetero)aryl chlorides. Amongst the alkoxide and amide counterions investigated, tert-butoxide was the most effective in inhibiting the homocoupling of arylmagnesiums. This journal is the Partner Organisations 2014.

Synthesis and reactivity of solid-supported organotrifluoroborates in suzuki cross-coupling

Solid-supported organotrifluoroborates were prepared in high yields by ion exchange with Amberlyst resins. The reactivity of solid supported aryltrifluoroborates was evaluated in Suzuki-Miyaura couplings with numerous aryl bromide partners. Electron-rich

Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts

The Suzuki-Miyaura coupling of phenol diazonium salts and aryl trifluoroborates yields 4-hydroxybiaryls in a protecting group-free synthesis. The Royal Society of Chemistry 2011.