Pd(OAc)2‐Catalyzed Carbonylation of Amines.

Orito, Kazuhiko; Miyazawa, M.; Nakamura, Takatoshi; Horibata, Akiyoshi; Ushito, Harumi; Nagasaki, Hideo; Yuguchi, Motoki; Yamashita, Satoshi; Yamazaki, Tetsuro; Tokuda, Masao

doi:10.1002/chin.200648053

Cited by 141 publications

(9 citation statements)

References 29 publications

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“…For example, oxidative carbonylation could occur with the amine leading to reduction of the metal center. [40][41] The increased size of the particles using a chloride precursor instead of an acetylacetonate has been reported previously with platinum alloys. 27 The particles formed without the carbonyl are generally spherical, lacking a distinct shape, which is indicative of only having a single surfactant in solution which is not interacting strongly with any particular surface facet of the particles.…”

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confidence: 92%

Synthesis and Characterization of Branched fcc/hcp Ruthenium Nanostructures and Their Catalytic Activity in Ammonia Borane Hydrolysis

AlYami

LaGrow

Anjum

et al. 2018

Crystal Growth & Design

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Several systems have shown the ability to stabilize uncommon crystal structures during the synthesis of metallic nanoparticles. By tailoring the nanoparticle crystal structure, the physical and chemical properties of the particles can also be controlled. Herein, we synthesized branched nanoparticles of mixed fcc/hcp ruthenium, which were formed using tungsten carbonyl [W(CO) 6 ] as both a reducing agent and a source of carbon monoxide. The branched particles were formed from multiple particulates off a central core. Highresolution transmission electron microscopy (HRTEM) clearly showed that the branched structures consisted of aligned hcp crystal domains, a mixture of fcc and hcp crystal domains with several defects and misalignments, and particles that contained multiple cores and branches. Branched particles were also formed with molybdenum carbonyl [Mo(CO) 6 ], and faceted particles of hcp and fcc were formed with rhenium carbonyl [Re 2 (CO) 10 ] as a carbon monoxide source. Without metal carbonyls, small particles of spherical hcp ruthenium were produced, and their size could be controlled by the selection of the precursor. The ruthenium nanoparticles were tested for ammonia borane hydrolysis; the branched nanoparticles were more reactive for catalytic hydrogen evolution than the faceted fcc/hcp nanoparticles or the spherical hcp nanoparticles. This work showcases the potential of crystal phase engineering of transition metal nanoparticles by different carbon monoxide precursors for tailoring their catalytic reactivity.P hysical and chemical properties, such as magnetism and catalytic activity, are intrinsically related to the crystal structure of nanomaterials. 1−3 Over the past two decades, a variety of noble metals have been produced in uncommon or previously unknown crystal structures, including Au, Ag, Pd, Rh, and Ru. 4 For example, face-centered cubic ( fcc) Ru nanoparticles were synthesized by Kitagawa et al., showing increased catalytic activity toward CO oxidation at larger particle sizes over nanoparticles made of the common crystal structure for Ru, i.e., hexagonal close packed (hcp). 5 Further work with fcc Ru and fcc Ru@Pt demonstrated enhanced catalytic properties over hcp Ru in the hydrogen evolution reaction, 6,7 hydrogen oxidation reaction, 8 and oxygen evolution reaction. 9 Nanoframes of fcc Ru were also reported to exhibit increased activity in the ammonium hydrolysis reaction compared to nanowires of hcp Ru. 6 These results indicate that fcc Ru is a promising system for increasing the activity of Ru catalysts. Shape-controlled fcc Ru nanoparticles have been synthesized as cages, frames, and cubes, using a core of a second metal as a template. 6,9,10 Branched or hierarchical nanoparticles have shown great promise in the stabilization of uncommon crystal structures because the reactions generally have multiple growth stages giving rise to complex morphologies. 11−14 Another common

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confidence: 92%

Synthesis and Characterization of Branched fcc/hcp Ruthenium Nanostructures and Their Catalytic Activity in Ammonia Borane Hydrolysis

AlYami

LaGrow

Anjum

et al. 2018

Crystal Growth & Design

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“…[30][31][32][33] It is notwithstanding that the development of selective and practical approach to construct this seemingly simple heterocyclic system is not always trivial. [34][35][36][37][38] In view of the readily accessible characters of starting materials and step economy, direct C-H bond carbonylation of benzylic amines [39][40][41][42] and monoreduction of phthalimide analogues 43,44 have been developed, but nonnegligible limitations are still remained.…”

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confidence: 99%

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

Zhang¹,

Zhao²,

Zhu³

et al. 2021

Preprint

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Isoindolinone is a class of versatile N-heterocycles embedded in many bioactive molecules and natural products. The invention of new methods to synthesize these heterocyclic compounds with easily accessible chemicals is always attractive. Herein, a conceptually novel approach to access this bicyclic system via isonitrile insertion enabled 1,4-pallaidum shift is described. Compared with conventional isonitrile participated C-H bond activation, both carbon and nitrogen atoms in isonitrile moiety are engaged in new bond formation. Notably, two different isoindolinones can be obtained selectively by switching the bases employed. Mechanistic studies including DFT calculations have shed lights on the reaction mechanism and explained the selectivity led to different products. Moreover, the power of current benzolactamization is further demonstrated by providing concise routes to key intermediates of indoprofen, indobufen, aristolactams, lennoxamine and falipamil.

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“…H NMR (300 MHz, CDCl 3 ): δ = 8.16(d, J = 7.5 Hz, 1 H), 1 H), 7.35 (d, J = 7.4 Hz, 1 H), 7.20(d, J = 7.5 Hz, 1 H), 4.00 (t, J = 6.3 Hz, 2 H), 3.00 (t, J = 6.1 Hz, 2 H), 1.59 (s, 9 H). 13 C NMR (75 MHz, CDCl 3 ): δ = 163.28, 152.50, 139.08, 132.33, 128.94, 128.82, 126.74, 126.63, 82.44, 43.97, 27.77, 27.59.2-Tosyl-3,4-dihydroisoquinolin-1(2H)-one (2e) 3bWhite solid; yield: 272 mg (90%); mp 135-137°C.…”

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confidence: 99%

“…13 C NMR (75 MHz, CDCl 3 ): δ = 173.57, 165.62, 140.17, 133.27, 129.42, 128.95, 127.26, 41.63, 28.04, 27.50.2-Benzyl-3,4-dihydro-1(2H)-isoquinolinone (2g) 8aColorless oil; yield: 200 mg (84%). 1 H NMR (300 MHz, CDCl 3 ): δ = 8.15(d, J = 7.5 Hz, 1 H), 7 H), 7.15 (d, J = 7.5 Hz, 1 H), 4.80 (s, 2 H), 3.48 (t, J = 6.6 Hz, 2 H), 2.93 (t, J = 6.6 Hz, 2 H). 13 C NMR (75 MHz, CDCl 3 ): δ = 164.24, 137.84, 137.20, 131.41, 129.12, 128.35, 128.11, 127.75, 127.15, 126.73, 126.67, 50.17, 45.10, 27.76. tert-Butyl 6,7-Dimethoxy-1-oxo-3,4-dihydroisoquinoline-2(1H)-carboxylate (2h)20 White solid; yield: 265 mg (86%); mp 124-127°C.1 H NMR (400 MHz, CDCl 3 ): δ = 7.65 (s, 1 H), 6.64 (s, 1 H), 3.98 (t, J = 6.4 Hz, 2 H), 3.94 (s, 3 H), 3.91 (s, 3 H), 2.94 (t, J = 6.2 Hz, 2 H), 1.59 (s, 9 H).…”

mentioning

confidence: 99%

A Simple and Effective Synthesis of Benzolactones and Benzolactams by Noncatalytic Benzylic Oxidation of Cyclic Benzylic Ethers and N-Protected Cyclic Benzylic Amines with Sodium Chlorite as an Oxidant

Song

Zhang

2012

Synthesis

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Pd(OAc)₂‐Catalyzed Carbonylation of Amines.

Cited by 141 publications

References 29 publications

Synthesis and Characterization of Branched fcc/hcp Ruthenium Nanostructures and Their Catalytic Activity in Ammonia Borane Hydrolysis

Synthesis and Characterization of Branched fcc/hcp Ruthenium Nanostructures and Their Catalytic Activity in Ammonia Borane Hydrolysis

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

A Simple and Effective Synthesis of Benzolactones and Benzolactams by Noncatalytic Benzylic Oxidation of Cyclic Benzylic Ethers and N-Protected Cyclic Benzylic Amines with Sodium Chlorite as an Oxidant

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Pd(OAc)2‐Catalyzed Carbonylation of Amines.

Cited by 141 publications

References 29 publications

Synthesis and Characterization of Branched fcc/hcp Ruthenium Nanostructures and Their Catalytic Activity in Ammonia Borane Hydrolysis

Synthesis and Characterization of Branched fcc/hcp Ruthenium Nanostructures and Their Catalytic Activity in Ammonia Borane Hydrolysis

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

A Simple and Effective Synthesis of Benzolactones and Benzolactams by Noncatalytic­ Benzylic Oxidation of Cyclic Benzylic Ethers and N-Protected Cyclic Benzylic Amines with Sodium Chlorite as an Oxidant

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Pd(OAc)₂‐Catalyzed Carbonylation of Amines.

A Simple and Effective Synthesis of Benzolactones and Benzolactams by Noncatalytic Benzylic Oxidation of Cyclic Benzylic Ethers and N-Protected Cyclic Benzylic Amines with Sodium Chlorite as an Oxidant