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Academic papers

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カルコゲン結合を利用した触媒反応ー珍しい相互作用による新しい有機合成

荻原陽平, 坂井教郎

化学(化学同人) 2019, 74, 66-67. (最新のトピックス)


Sulfenylation of arenes and olefins with acidic sulfenamides

Shimizu, M.; Suzuki, S.; Tanaka, S.; Ando, W.; Sakai, N.

Phosphorus, Sulfur, Silicon, Relat. Elem. 2019, 194, 764-767. (proceeding)

DOI:  10.1080/10426507.2019.1603724



Catalytic C–H/C–F Coupling of Azoles and Acyl Fluorides

Ogiwara, Y,; Iino, Y.; Sakai, N.

Chem Eur. J. 2019, 25, 6513-6516.

DOI: 10.1002/chem.201901219

Selected as Most Downloaded Paper in 2018-2019


Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

Sakai, N.; Maeda, H.; Ogiwara, Y.

Synthesis 2019, 51, 2323-2330.

DOI: 10.1055/s-0037-1610869



Palladium(II)/Copper(II)-Catalyzed C-H Sulfidation or Selenation of Arenes Leading to Unsymmetrical Sulfides and Selenides

Nishino, K.; Tsukahara, S.; Ogiwara, Y.; Sakai, N.

Eur. J. Org. Chem. 2019, 1588-1593.

DOI: 10.1002/ejoc.201801765

Selected as Most Downloaded Paper in 2018-2019


2019

citation number (over 50) searched by SciFinder

6.2.2020 Update

2019~2015


Construction of N-Heterocyclic Systems Containing a Fully

Substituted Allylic Carbon by Palladium/Phosphine Catalysis

Ogiwara, Y.; Suzuki, Y.; Sato, K.; Sakai, N.

Org. Lett. 2018, 20, 6965-6969.

DOI: 10.1021/acs.orglett.8b03127



Group-4-Metallocene-Difluoride/Palladium Bimetallic Catalysts for the

Reductive Cross-Coupling of Alkynes with Aryl Iodides and Bromides

Takahashi, K.; Morishita, H.; Ogiwara, Y.; Sakai, N.

J. Org. Chem. 2018, 83, 13734-13742.

DOI: 10.1021/acs.joc.8b02055



Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via

Ligand-Controlled Decarbonylation

Ogiwara, Y.; Sakurai, Y.; Hattori, H.; Sakai, N.

Org. Lett. 2018, 20, 4204-4208. 

DOI: 10.1021/acs.orglett.8b01582



Palladium(II)-Catalyzed Synthesis of Dibenzothiophenes from

2-Biphenylyl Disulfides via C-H functionalization

Nishino, K.; Ogiwara, Y.; Sakai, N.

Chem. Eur. J. 2018, 24, 10971-10974.

DOI: 10.1002/chem.201802475



Indium-Catalyzed Direct Conversion of Lactones into Thiolactones Using

a Disilathiane as a Sulfur Source

Ogiwara, Y.; Takano, K.; Horikawa, S.; Sakai, N.

Molecules (Special Issue) 2018, 23, 1339-1349.

DOI: 10.3390/molecules23061339 (open access)



Indium-catalyzed Direct Conversion of Dibenzyl Ethers to Dibenzyl

Sulfides Using Elemental Sulfur and a Hydrosilane and Its Application to

the Preparation of Benzyl Selenides

Sakai, N.; Takada, K.; Katayama, M.; Ogiwara, Y.

Chem. Lett. 2018, 47, 791-793.

DOI: 10.1246/cl.180242



Palladium-Catalyzed Reductive Coupling Reaction of Terminal Alkynes

with Aryl Iodides Utilizing Hafnocene Difluoride as a Hafnium Hydride

Precursor Leading to trans-Alkenes

Takahashi, K.; Ogiwara, Y.; Sakai, N.

Chem. Asian J. 2018, 13, 809-814.

DOI: 10.1002/asia.201701775



Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and

Selenolactones in the Presence of Elemental Sulfur and Selenium

Sakai, N.; Horikawa, S.; Ogiwara, Y.

Synthesis 2018, 50, 565-574.

DOI: 10.1055/s-0036-1591849



Copper-Catalyzed Production of Daryl Sulfides Using Aryl Iodides and

a Disilathiane

Ogiwara, Y.; Maeda, H.; Sakai, N.

Synlett 2018, 29, 655-657.

DOI: 10.1055/s-0036-1591723   as Thieme News-Archive 2017



インジウム触媒とヒドロシランを用いた還元的分子変換を中心とする有機合成

(Indium-Catalyzed Reductive Molecular Transformation Using Hydrosilanes)

荻原陽平, 坂井教郎

有機合成化学協会誌 2018, 76, 21-36.

DOI: 10.5059/yukigoseikyokaishi.76.21

2018


One-pot Two-step Conversion of Aromatic Carboxylic Acids and Esters

to Aromatic Aldehydes Via Indium-Catalyzed Reductive

Thioacetalization and Desulfurization

Sakai, N.; Minato, K.; Ogiwara, Y.

Tetrahedron Lett. 2017, 58, 4563-4567.

DOI: 10.1016/j.tetlet.2017.10.050



Copper-Catalyzed Cyanation of Aryl Iodides Using Nitromethane

Ogiwara, Y.; Morishita, H.; Sasaki, M.; Imai, Y.; Sakai, N.

Chem. Lett. 2017, 46, 1736-1739.

DOI: 10.1246/cl.170798



Palladium-Catalyzed Intramolecular Cyclization of Alkynoic Acids To

Form Vinyl Dioxanones Bearing a Quaternary Allylic Carbon

Ogiwara, Y.; Sato, K.; Sakai, N.

Org. Lett. 2017, 19, 5296-5299.

DOI: 10.1021/acs.orglett.7b02572



Green Preparation of Dibenzothiophene Derivatives Using 2-Biphenylyl

Disulfides in the Presence of Molecular Iodine and Its Application

to Dibenzoselenophene Synthesis

Nishino, K.: Ogiwara, Y.; Sakai, N.

Eur. J. Org. Chem. 2017, 5892-5895.

DOI: 10.1002/ejoc.201701155



Acid Fluorides as Acyl Electrophiles in Suzuki-Miyaura Coupling

Ogiwara, Y.; Sakino, D.; Sakurai, Y.; Sakai, N.

Eur. J. Org. Chem. 2017, 4324-4327.

DOI: 10.1002/ejoc.201700917



Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with

Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization

Nishino, K.: Minato, K.: Miyazaki, T.: Ogiwara, Y.; Sakai, N.

J. Org. Chem. 2017, 82, 3659-3665.

DOI: 10.1021/acs.joc.7b00170



Reaction of 2-alkylidene-3,1-benzoxathiin-4-ones with nitrones

Shimizu, M.; Yamanaka, M.; Kurita, K.; Tanaka, S.; Ando, W.; Sakai, N.

Phosphorus, Sulfur, Silicon, Relat. Elem. 2017, 192, 249-251. (proceeding)

DOI: 10.1080/10426507.2016.1255620



Cyclization of 2-(N-pyrrolylsulfenyl)benzoic acids for the synthesis of

pyrrolo[1,2-b][1,2]benzothiazin-10-ones

Masuda, K.; Kato, D.; Tanaka, S.; Ando, W.; Sakai, N.; Shimizu, M.

Phosphorus, Sulfur, Silicon, Relat. Elem. 2017, 192, 235-236. (proceeding)

DOI: 10.1080/10426507.2016.1255618



Carboxamides as an N-Alkylating Reagent of Secondary Amines in

Indium-Catalyzed Reductive Amination with a Hydrosilane
Ogiwara, Y.; Shimoda, W.; Ide, K., Nakajima, T.; Sakai, N.

Eur. J. Org. Chem. 2017, 2866-2870. 

DOI: 10.1002/ejoc.201601629

Selected as Very Important Paper (VIP) and Cover Picture of EurJOC



Determination of binding modes and binding constants for the

complexes of 6H-pyrido[4,3-b]carbazole derivatives with DNA

Shimazu, A.: Kawagoshi, M.; Takeda, S.; Kurasaki, H.; Kato, A.; Morii, N.;

Sakai, N.; Konakahara, T.

Bioorg. Med. Chem. 2017, 25, 1094-1112. 

DOI: 10.1016/j.bmc.2016.12.031



Indium-Catalyzed Reduction of a Nitroarene Using a Hydrosilane:

A Selective Reduction Strategy for the Efficient Synthesis of Indoprofen

Ogiwara, Y.; Sakurai, Y.; Sakai, N.

Chem. Lett. 2017, 46, 240-242. 

DOI: 10.1246/cl.161008



One-Pot Preparation of Pyrrole Derivatives via the Copper-Catalyzed

[4+1] Annulation of Propargylic Amines with Ethyl Glyoxylate and

Phenylglyoxal in the Presence of Piperidine

Sakai, N.; Suzuki, H.; Hori, H,; Ogiwara, Y.

Tetrahedron Lett. 2017, 58, 63-66. 

DOI: 10.1016/j.tetlet.2016.11.097



Cobalt(II)–Catalyzed Oxidative Coupling of Aromatic Tertiary Amines

with Enol Silyl Ethers Leading to β-Aminoketone Derivatives

Sakai, N.; Muraoka, T.; Matsumoto, S.; Mutsuro, A.; Ogiwara, Y.

Synlett 2017, 28, 343-346. 

DOI: 10.1055/s-0036-1588097

2017

2016


Cobalt-Catalyzed Oxidative Annulation of Aromatic Tertiary Amines with

Electron-Deficient Maleimides Leading to Tetrahydroquinoline Derivatives

Sakai, N.; Matsumoto, S.; Ogiwara, Y.

Tetrahedron Lett. 2016, 57, 5449-5452.

DOI: 10.1016/j.tetlet.2016.10.071



Gallium-Catalyzed Reductive Lactonization of γ-Keto Acids with

a Hydrosilane

Sakai, N.; Horikawa, S.; Ogiwara, Y.

RSC Adv. 2016, 6, 81763-81766.

DOI: 10.1039/C6RA19286F



Indium(III) Isopropoxide as a Hydrogen Transfer Catalyst for Conversion

of Benzylic Alcohols into Aldehydes or Ketones via Oppenauer Oxidation

Ogiwara, Y.; Ono, Y.; Sakai, N.

Synthesis, 2016, 48, 4143-4148.

DOI: 10.1055/s-0035-1562542



Indium-Catalyzed Reductive Three-Component Coupling Reaction of

Aliphatic/Aromatic Carboxylic Acids with t-Butyl Mercaptan Leading to

Unsymmetrical Dialkyl Sulfides

Sakai, N.; Yoshimoto, S.; Miyazaki, T.; Ogiwara, Y.

Tetrahedron Lett. 2016, 57, 3117-3120.

DOI: 10.1016/j.tetlet.2016.06.001



Synthesis and Cytotoxic Activity of Novel 11-Methyl-6H-Pyrido[4,3-b]

Carbazole Derivatives Linked to Amine, N-Methylurea, and

N-Methyl-N-Nitrosourea Moieties with Various Types of Carbamoyl

Tethers at the C-5 Atom

Kato, A.; Nagatsuka, Y.; Hiratsuka, T.; Kiuchi, S.; Iwase, Y.; Okuno, Y.;

Tsukamoto, T.; Kiran, Y. B.; Sakai, N.; Konakahara, T.

Tetrahedron 2016, 72, 4258-4272.

DOI: 10.1016/j.tet.2016.05.068



Palladium-Catalyzed Coupling of Benzoyl Halides with Aryltrifluorosilanes

Leading to Diaryl Ketones

Ogiwara, Y.; Maegawa, Y.; Sakino, D.; Sakai, N.

Chem. Lett. 2016, 45, 790-792.

DOI: 10.1246/cl.160223



Copper-Catalyzed [3+2] Annulation of Propargylic Acetates with Anilines

in the Presence of Trimethylsilyl Chloride Leading to 2,3-disubstituted

Indoles via an Aza-Claisen Rearrangement

Sakai, N.; Enomoto, K.; Takayanagi, M.; Konakahara, T.; Ogiwara, Y.

Tetrahedron Lett. 2016, 57, 2175-2178.

DOI: 10.1016/j.tetlet.2016.04.007



Production of Quaternary α-Aminonitriles by Means of Indium-Catalyzed

Three-Component Reaction of Alkynes, Amines, and Trimethylsilyl

Cyanide

Hamachi, Y.; Katano, M.; Ogiwara, Y.; Sakai, N.

Org. Lett. 2016, 18, 1634-1637.

DOI: 10.1021/acs.orglett.6b00508



Synthesis and in vitro Antitumor Activity of 9-Hydroxyellipticine

Derivatives with Glucose Conjugation via Triazolylmethyl Succinate

Linker

Sato, N.; Kawai, Y.; Akaba, Y.; Honma, S.; Sakai, N.; Konakahara, T.

Heterocycles 2016, 92, 664-679.

DOI: 10.3987/COM-16-13404



Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols:

An Approach to the Diverse Synthesis of Sulfides

Miyazaki, T.; Kasai, S.; Ogiwara, Y.; Sakai, N.

Eur. J. Org. Chem. 2016, 1043-1049.

DOI: 10.1002/ejoc.201501559



Indium-Catalyzed Direct Preparation of Dibenzyl Sulfides from Benzyl

Alcohols and Elemental Sulfur with a Hydrosilane and Its Application to

the Preparation of Dibenzyl Selenide

Miyazaki, T.; Katayama, M.; Yoshimoto, S.; Ogiwara, Y.; Sakai, N.

Tetrahedron Lett. 2016, 57, 676-679.

DOI: 10.1016/j.tetlet.2015.12.109



Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for

Selective Production of Lactams versus Cyclic Amines by Switching of

the Indium Catalyst

Ogiwara, Y.; Uchiyama, T.; Sakai, N.

Angew. Chem. Int. Ed. 2016, 55, 1864-1867.

DOI: 10.1002/anie.201509465 (61 citation number by Sep 2020)


Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to

Alkynyl Ketones by Using Indium(III) Bromide

Ogiwara, Y.; Kubota, M.; Kurogi, K.; Konakahara, T.; Sakai, N.

Chem. Eur. J. 2015, 21, 18598-18600.

Cited by SYNFACTS 2015, 12, 0188-0188

DOI:  10.1002/chem.201504255



Indium-Catalyzed Reduction of Secondary Amides with a Hydrosiloxane

Leading to Secondary Amines

Sakai, N.; Takeoka, M.; Kumaki, T.; Asano, H.; Konakahara, T.; Ogiwara, Y.

Tetrahedron Lett. 2015, 56, 6448-6451. 

DOI: 10.1016/j.tetlet.2015.09.148



One-pot Synthesis of Tetralin Derivatives From 3-Benzoylpropionic Acids:

Indium-Catalyzed Hydrosilylation of Ketones and Carboxylic Acids and

Intramolecular Cyclization

Sakai, N.; Kobayashi, T.; Ogiwara Y.

Chem. Lett. 2015, 44, 1503-1505. 

DOI: 10.1246/cl.150686



Indium(III)-Catalyzed Reduction of Nitrobenzenes to Anilines: Scope and

Limitations

Sakai, N.; Asama, S.; Konakahara, T.; Ogiwara, Y.

Synthesis 2015, 47, 3179-3185. 

DOI: 10.1055/s-0034-1378850



2価パラジウム錯体からの還元的脱離によるsp2 炭素-ハロゲン結合形成と

最近の展開

荻原陽平

有機合成化学協会誌 2015, 73, 1020-1021. (Review de Debut)

DOI: 10.5059/yukigoseikyokaishi.73.1020



Copper(II)-Catalyzed Oxidative Nitrosation of Secondary and Tertiary Amines with Nitromethane Under an Oxygen Atmosphere

Sakai, N.; Sasaki, M.; Ogiwara, Y.

Chem. Commun. 2015, 51, 11638-11641.

DOI: 10.1039/C5CC03675E



A Novel Macroreticular-Type Fluorous Polystyrene Resin and Its

Application to the Synthesis of a 3-Amino-β-Carboline Derivative with

N-Methyl-N-Nitrosourea Conjugation via Fluorous Solid-Phase Reaction:

A Comparative Study of Fluourous-Solid, Solid-, and Liquid-Phase

Reactions

Suzuki, K.; Kumagai, M.; Utsunomiya, M.; Sakai, N.; Konakahara, T.

Tetrahedron 2015, 71, 4999-5012.

DOI: 10.1016/j.tet.2015.05.072



Copper(I)-Catalyzed Coupling Reaction of Aryl Boronic Acids with N,O-

Acetals and N,N-Aminals Under Atmosphere Leading to α-Aryl Glycine

Derivatives and Diarylmethylamine Derivatives

Sakai, N.; Hori, H.; Yoshida, Y.; Konakahara, T.; Ogiwara, Y.

Tetrahedron 2015, 71, 4722-4729.

DOI: 10.1016/j.tet.2015.05.068



Indium(III)-Catalyzed Reductive One-Pot Synthesis of Thioethers from

Aromatic Aldehydes and Elemental Sulfur

Miyazaki, T.; Nishino, K.; Konakahara, T.; Sakai, N.

Phosphorus, Sulfur, Silicon, Relat. Elem. 2015, 190, 1378-1379.

(proceeding)

DOI: 10.1080/10426507.2015.1036990



Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and

Activated Methylenes Using Acetic Anhydride as a Promoter

Ogiwara, Y.; Takahashi, K.; Kitazawa, T.; Sakai, N.

J. Org. Chem. 2015, 80, 3101-3110.

DOI: 10.1021/acs.joc.5b00011



Indium(III)-Catalyzed Reductive Monoalkylation of Electron-Rich

Benzenes with Aliphatic Carboxylic Acids Leading to Arylalkane

Derivatives

Moriya, T.; Takayama, K.; Konakahara, T.; Ogiwara, Y.; Sakai, N.

Eur. J. Org. Chem. 2015, 2277-2281.

DOI: 10.1002/ejoc.201500096



Copper(II)-Catalyzed [4+1] Annulation of Propargylamines with N,O-

Acetals: Entry to the Synthesis of Polysubstituted Pyrrole Derivatives

Sakai, N.; Hori, H.; Ogiwara, Y.

Eur. J. Org. Chem. 2015, 1905-1909.

DOI: 10.1002/ejoc.201500098



Indium-Catalyzed Reductive Sulfidation of Aromatic Carboxylic Acids and

Aldehydes with Elemental Sulfur to Prepare Symmetrical Benzyl Sulfides

Miyazaki, T.; Nishino, K.; Yoshimoto, S.; Ogiwara, Y.; Sakai, N.

Eur. J. Org. Chem. 2015, 1991-1994.

DOI: 10.1002/ejoc.201403567



One-Pot Preparation of Alkyl Iodides from Esters by Indium-Catalyzed

Reductive Cleavage of a Carbon-Oxygen Bond

Sakai, N.; Matsushita, Y.; Konakahara, T.; Ogiwara, Y.; Hirano, K.

Eur. J. Org. Chem. 2015, 1591-1595.

DOI: 10.1002/ejoc.201403539

2015