Search results for: Akiya Ogawa

Items from 1 to 20 out of 117 results

article

Transition‐Metal‐Catalyzed Addition of Organosulfur Compounds to Alkynes and Alkenes: Catalysis and Catalyst Poisons

Yuki Yamamoto, Akiya Ogawa

Chemistry – A European Journal > 29 > 64 > n/a - n/a

The addition of heteroatom compounds to alkynes and alkenes is an atom‐efficient method of carbon‐heteroatom bond formation and is widely used as a fundamental synthetic method for the construction of functional molecules. Nevertheless, examples of transition‐metal‐catalyzed addition reactions of group 16 heteroatom compounds to carbon‐carbon unsaturated bonds have been limited due to the widespread...

article

Sequential Intramolecular Diels–Alder Reaction of 3‐Heteroaryl‐2‐propenylamides of Ethenetricarboxylate

Hirotaka Sugiura, Shoko Yamazaki, Akiya Ogawa

Journal of Heterocyclic Chemistry > 56 > 9 > 2592 - 2603

The reaction of 1,1,2‐ethenetricarboxylic acid 1,1‐diethyl ester with E‐3‐(2‐furyl)‐2‐propenylamines under the amide condensation conditions (EDCI/HOBt/Et₃N) on heating at 80–110°C afforded cis‐fused tricyclic compounds, furo[2,3‐f]isoindoles as major product. On the other hand, the reaction with E‐3‐(3‐furyl)‐2‐propenylamines afforded trans‐fused tricyclic compounds predominantly. The formation of...

article

Reductive Rearrangement of Tetraphenyldiphosphine Disulfide To Trigger the Bisthiophosphinylation of Alkenes and Alkynes

Yuki Sato, Misaki Nishimura, Shin‐ichi Kawaguchi, Akihiro Nomoto, more

Chemistry – A European Journal > 25 > 27 > 6797 - 6806

The facile synthesis of organophosphorus compounds is of great importance for the development of new synthetic methods by using air‐stable sources of phosphorus. In this respect, a synthetic method that is based on a reductive rearrangement and is capable of converting air‐stable pentavalent phosphorus compounds into reactive trivalent phosphorus compounds is a powerful tool. Tetraphenyldiphosphine...

article

Synthesis of Bis(phosphanyl)alkane Monosulfides by the Addition of Diphosphane Monosulfides to Alkenes under Light

Yuki Sato, Shin‐ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa

Chemistry – A European Journal > 25 > 9 > 2295 - 2302

Bis‐phosphanated compounds are regarded as the most ubiquitous privileged ligand structures in transition‐metal catalysis. The development of highly atom economical reactions is of great importance for their syntheses because less atom economical methods often require complicated purification procedures under inert atmospheres to remove excess starting materials and byproducts. Herein, the photoinduced...

article

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Yuki Yamamoto, Fumiya Sato, Shintaro Kodama, Akihiro Nomoto, more

Heteroatom Chemistry > 29 > 5-6 > n/a - n/a

The reactivity of diaryl ditelluride and diaryl telluride toward aryl radicals was studied in detail. Diphenyl ditelluride underwent a bimolecular homolytic substitution (S_H2) reaction with a phenyl radical generated from phenylhydrazine in the air, to afford diphenyl telluride in excellent yield. Based on this diphenyl telluride synthesis, a one‐pot synthesis of unsymmetrical diaryl tellurides was...

article

Intramolecular Cyclization of 3,3‐Diarylpropenylamides of Electron‐Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

Hirotaka Sugiura, Shoko Yamazaki, Kakeru Go, Akiya Ogawa

European Journal of Organic Chemistry > 2019 > 1 > 204 - 220

Intramolecular Diels–Alder reactions of various 3,3‐diarylpropenylamides of electron‐deficient alkenes to give hexahydrobenzo[f]isoindoles were investigated. Reaction of 1,1,2‐ethenetricarboxylic acid 1,1‐diethyl ester with 3,3‐diaryl‐2‐propen‐1‐amines under the amide formation conditions gave the tricyclic compounds in sequential processes involving intramolecular Diels–Alder reaction. The reaction...

article

Synthesis, characterization, thermal and luminescent properties of thiophenol-functionalized platinum(II) bis(acetylide) complexes

Md. Mostafizur Rahman, Shishir Kanti Pramanik, Dababrata Paul, M. A. A. Shofi Uddin Sarkar, more

Transition Metal Chemistry > 2019 > 44 > 3 > 247-252

Two thiophenol-functionalized trans-platinum(II) bis(acetylide) complexes, having one thiophenol moiety in each alkenyl backbone with general formula trans-[(PPh₃)₂Pt{C≡C–Ar–CH=CH(SC₆H₅)}₂], (2a–2b), (Ar = phenylene or 2,5-dimethylphenylene), were synthesized in good yields and good regioselectivities. Compared to the absorption bands of the trans-platinum(II) bis(acetylide) complexes 1, the positions...

article

Mechanistic study of silica-gel or FeCl₃-promoted ring-opening aromatization of 7-oxanorborna-2,5-dienes affording 2-bromo-3-hydroxybenzoate derivatives

Motohiro Sonoda, Ayu Ikeda, Hiroyuki Shinohara, Naoya Hayagane, more

Research on Chemical Intermediates > 2019 > 45 > 1 > 13-21

One-pot synthesis of 2-bromo-3-hydroxybenzoates by the Diels–Alder reaction of furans with bromoalkyne and the subsequent ring-opening aromatization was studied by means of deuterium-labeling experiments. The residual protons in silica gel were considered to be the hydrogen source of the hydroxy group of products under the silica gel-promoted condition. The deuterium-labeling experiment revealed a...

article

Synthesis and crystal structures of phenylalanine ester-introduced palladium(II) and platinum(II) complexes and their cytotoxicities

Akihiro Nomoto, Nozomi Sakamoto, Yuta Sakai, Keisuke Fukumoto, more

Research on Chemical Intermediates > 2019 > 45 > 1 > 3-12

Phenylalanine ester-introduced palladium(II) and platinum(II) complexes were synthesized. Taking advantage of the formation of Schiff bases by amino acids as an intermediate, the pyridylimine moiety coordinated to a metal center. Single crystals of each complex were obtained successfully, and their molecular structures were clarified in detail. The Pd(II) complex showed remarkable cytotoxicity compared...

article

Synthesis and characterization of a biphenyl-linked hemicryptophane and an endohedral cobalt(II) complex

Yoshimasa Makita, Tomofumi Danno, Keisuke Ikeda, Hsien-Han Lee, more

Tetrahedron Letters > 2017 > 58 > 48 > 4507-4509

Hemicryptophanes are covalent molecular cages, constructed from a cyclotriveratrylene-based host unit and a functional unit linked by covalent spacers, which have been designed to accommodate endohedral functionalities in the cavity. In this study, the synthesis and characterization of the rigid, biphenyl-linked hemicryptophane 1 were investigated by NMR, ESI-MS, and X-ray crystallography. The structure...

article

Front Cover: Hydroiodination‐Triggered Cascade Reaction with I₂/PPh₃/H₂O: Metal‐Free Access to 3‐Substituted Phthalides from 2‐Alkynylbenzoates (Eur. J. Org. Chem. 36/2017)

Shin‐ichi Kawaguchi, Kentaro Nakamura, Kotaro Yamaguchi, Yuki Sato, more

European Journal of Organic Chemistry > 2017 > 36 > 5315 - 5315

The Front Cover shows a cascade reaction under metal‐free conditions. The reaction depicts a waterfall (cascade) and a place that is not usually associated with a metal (forest). Easily available reagents, i.e., triphenylphosphine, iodine, and water, trigger the cascade reaction, which includes desilylation, hydroiodination, cyclization, and reduction to give phthalides from 2‐(trimethylsilylalkynyl)benzoates...

article

Hydroiodination‐Triggered Cascade Reaction with I₂/PPh₃/H₂O: Metal‐Free Access to 3‐Substituted Phthalides from 2‐Alkynylbenzoates

Shin‐ichi Kawaguchi, Kentaro Nakamura, Kotaro Yamaguchi, Yuki Sato, more

European Journal of Organic Chemistry > 2017 > 36 > 5343 - 5346

Phthalide is an important scaffold found in several biologically active compounds. Therefore, effective methods for the synthesis of phthalides are strongly desired. Herein, we describe the metal‐free synthesis of 3‐substituted phthalides by the reductive hydroiodination of 2‐alkynylbenzoates through an I₂/PPh₃/H₂O‐triggered cascade reaction. A variety of 3‐substituted phthalides were synthesized...

article

Atom‐Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

Toshihide Taniguchi, Akinori Murata, Motonori Takeda, Takumi Mizuno, more

European Journal of Organic Chemistry > 2017 > 33 > 4928 - 4934

An atom‐economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals...

article

The PMe3-catalyzed addition of enantiomerically pure (−)-MenthylO(Ph)P(O)H to electron-deficient alkenes: an efficient way for the preparation of P-stereogenic compounds

Yuta Saga, Yuka Mino, Shin-ichi Kawaguchi, Daoqing Han, more

Tetrahedron: Asymmetry > 2017 > 28 > 1 > 84-89

A variety of P-stereogenic organophosphorus compounds can be readily prepared by stereoretentive addition. The PMe₃-catalyzed addition of optically active (−)MenthylO(Ph)P(O)H compounds to electron deficient alkenes occur stereospecifically, to produce the corresponding P-stereogenic adducts in high yields. By simply removing the volatiles under vacuum, spectroscopically pure products can be obtained...

article

Photoinduced metal-free diboration of alkynes in the presence of organophosphine catalysts

Aya Yoshimura, Yuki Takamachi, Kei Mihara, Tomokazu Saeki, more

Tetrahedron > 2016 > 72 > 48 > 7832-7838

In sharp contrast to the transition metal-catalyzed diboration of alkynes with diboron species such as B₂pin₂, which affords vicinal cis-diborated alkenes, the organophosphine-catalyzed addition of B₂pin₂ to alkynes proceeds under metal-free conditions upon photoirradiation to give the corresponding vicinal trans-diborated alkenes with good stereoselectivity. For example, the photoinduced diboration...

article

A tri-aromatic amide hemicryptophane host: synthesis and acetylcholine binding

Yoshimasa Makita, Natsuki Katayama, Hsien-Han Lee, Taro Abe, more

Tetrahedron Letters > 2016 > 57 > 46 > 5112-5115

Hemicryptophanes have been designed to include endohedral functionalities in the cavity, giving molecular receptors and catalysts. In this study, a tri-aromatic amide hemicryptophane was synthesized. The host–guest interactions with various types of tetraalkylammonium salts were investigated. The structure of the partial inclusion complex in which an acetylcholine molecule was encapsulated within...

article

Synthesis, spectroscopic characterization, thermal and luminescent properties of new organosulfur-functionalized platinum(II) bis(alkenylarylalkynyl) complexes

Md. Mostafizur Rahman, Muhammad Younus, Masnun Naher, Mostafa Kamal Masud, more

Journal of Organometallic Chemistry > 2016 > 818 > C > 185-194

A series of organosulfur-functionalized trans-platinum(II) bis(alkenylarylalkynyl) complexes, having one tolylthio moiety in each alkenyl backbone with general formula trans-[(PEt₃)₂Pt{CC-Ar-CHCH(SC₆H₄CH₃)}₂], (2a–2d), (where, Ar = phenylene, biphenylene, 2,5-dimethylphenylene, and 2,5-dimethoxyphenylene) were synthesized in good to excellent yields with good regioselectivity. As compared to the absorption...

article

Highly Selective Phosphinylphosphination of Alkenes with Tetraphenyldiphosphine Monoxide

Yuki Sato, Shin‐ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa

Angewandte Chemie > 128 > 33 > 9852 - 9855

In sharp contrast to tetraphenyldiphosphine, which does not add to carbon–carbon double bonds efficiently, its monoxide, [Ph₂P(O)PPh₂] can engage in a radical addition to various alkenes, thus affording the corresponding 1‐phosphinyl‐2‐phosphinoalkanes regioselectively, and they can be converted into their sulfides by treatment with elemental sulfur. The phosphinylphosphination proceeds by the homolytic...

article

Highly Selective Phosphinylphosphination of Alkenes with Tetraphenyldiphosphine Monoxide

Yuki Sato, Shin‐ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa

Angewandte Chemie International Edition > 55 > 33 > 9700 - 9703

article

An efficient base-catalyzed double addition of H-phosphine oxides to alkynes

Aya Yoshimura, Yuta Saga, Yuki Sato, Akiya Ogawa, more

Tetrahedron Letters > 2016 > 57 > 30 > 3382-3384

An efficient base-catalyzed double addition of H-phosphine oxides to alkynes is developed. In the presence of a catalytic amount of a base, the addition of various H-phosphine oxides to both aromatic and aliphatic alkynes took place efficiently to produce the corresponding bisphosphoryl compounds in excellent yields. This method provides an easy direct way to prepare bisphosphine oxides that are of...

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CARBON MONOXIDE (9)
ALKYNES (6)
RADICAL REACTIONS (6)
SULFUR (6)
CARBONYLATION (5)
CYCLOTRIVERATRYLENE (5)
DIELS–ALDER REACTION (4)
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ALKENES (2)
ALLENES (2)
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DESELENATION (2)
DISELENIDE (2)
FUNCTIONALIZATION (2)
HYDROIODINATION (2)
ONE-POT REACTION (2)
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OXIDATION (2)
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TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) (2)
THIOL (2)
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VINYL SELENIDE (2)
ZINC (2)
ANTI-MARKOVNIKOV ADDITION (1)
1,2-DIMETHOXYETHANE (1)
2-BROMO-3-HYDROXYBENZOATE (1)
3-HYDROXYANTHRANILATE (1)
3-HYDROXYBENZOATE (1)
3-HYDROXYPHTHALATE (1)
ACETYLCHOLINE (1)
ACID CHLORIDE (1)
AIR CONDITION (1)
ALKENYLARYLALKYNYL COMPLEX (1)
ALKENYLARYLALKYNYL COMPLEXES (1)
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AXLE (1)
BASE-CATALYSIS (1)
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INFONA - science communication portal

Search results for: Akiya Ogawa

Transition‐Metal‐Catalyzed Addition of Organosulfur Compounds to Alkynes and Alkenes: Catalysis and Catalyst Poisons

Sequential Intramolecular Diels–Alder Reaction of 3‐Heteroaryl‐2‐propenylamides of Ethenetricarboxylate

Reductive Rearrangement of Tetraphenyldiphosphine Disulfide To Trigger the Bisthiophosphinylation of Alkenes and Alkynes

Synthesis of Bis(phosphanyl)alkane Monosulfides by the Addition of Diphosphane Monosulfides to Alkenes under Light

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Intramolecular Cyclization of 3,3‐Diarylpropenylamides of Electron‐Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

Synthesis, characterization, thermal and luminescent properties of thiophenol-functionalized platinum(II) bis(acetylide) complexes

Mechanistic study of silica-gel or FeCl₃-promoted ring-opening aromatization of 7-oxanorborna-2,5-dienes affording 2-bromo-3-hydroxybenzoate derivatives

Synthesis and crystal structures of phenylalanine ester-introduced palladium(II) and platinum(II) complexes and their cytotoxicities

Synthesis and characterization of a biphenyl-linked hemicryptophane and an endohedral cobalt(II) complex

Front Cover: Hydroiodination‐Triggered Cascade Reaction with I₂/PPh₃/H₂O: Metal‐Free Access to 3‐Substituted Phthalides from 2‐Alkynylbenzoates (Eur. J. Org. Chem. 36/2017)

Hydroiodination‐Triggered Cascade Reaction with I₂/PPh₃/H₂O: Metal‐Free Access to 3‐Substituted Phthalides from 2‐Alkynylbenzoates

Atom‐Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

The PMe3-catalyzed addition of enantiomerically pure (−)-MenthylO(Ph)P(O)H to electron-deficient alkenes: an efficient way for the preparation of P-stereogenic compounds

Photoinduced metal-free diboration of alkynes in the presence of organophosphine catalysts

A tri-aromatic amide hemicryptophane host: synthesis and acetylcholine binding

Synthesis, spectroscopic characterization, thermal and luminescent properties of new organosulfur-functionalized platinum(II) bis(alkenylarylalkynyl) complexes

Highly Selective Phosphinylphosphination of Alkenes with Tetraphenyldiphosphine Monoxide

Highly Selective Phosphinylphosphination of Alkenes with Tetraphenyldiphosphine Monoxide

An efficient base-catalyzed double addition of H-phosphine oxides to alkynes

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