Original Papers / 原著論文

68

Aluminum-catalyzed direct conversion of lactones to selenolactones in the presence of elemental selenium and its application in the indium-catalyzed syntheses of dibenzyl selenides from benzyl acetates

*Norio Sakai, Yasushi Kino, Yohei Ogiwara, Kento Ishida

67

Selective O-Acylation of Enol Silyl Ethers with Acyl Fluorides Catalyzed by Fluoride Ions Derived from Potassium Fluoride and 18-Crown-6

*Norio Sakai, Kota Watanabe, Haruka Mori, Yuki Maegawa, Ryuki Takeuchi, Yohei Ogiwara, Kento Ishida

66.

Chemical Upcycling of PET into a Morpholine Amide as a Versatile Synthetic Building Block

*Yohei Ogiwara, Kotohiro Nomura

EurekAlert! (URL)

65

Synthesis of Two Types of 1,3-Diarylpropane Derivatives by Cobalt-Catalyzed Cycloaddition of 1,6-Diynes

Kento Ishida, Shu Mizusawa, Koji Nakamura, Yohei Ogiwara, *Norio Sakai

64

Depolymerization of Polyesters by Transesterification with Ethanol Using (Cyclopentadienyl)titanium Trichlorides

Yuriko Ohki, Yohei Ogiwara, *Kotohiro Nomura

63

Synthesis of Dithioacetals through Iodine-Promoted Insertion Reactions of Vinylsilane to Disulfides and its Application to Diselenoacetalization

*Norio Sakai, Kurumi Fukuda, Yohei Ogiwara, Kento Ishida

62

Disilathiane as a Sulfur Source for the Construction of Isothiochromenes and Benzo[b]thiophenes by Copper-Catalyzed endo-Selective Hydrothiolation

Takumi Nakajima, Ryuki Takeuchi, Keita Oomori, Kento Ishida, Yohei Ogiwara, *Norio Sakai

61

Phosphine-Catalyzed Acyl-Group Exchange Reaction of Carboxylic Acids and an Aroyl Fluoride

Hiroyuki Hattori, Kento Ishida, Yohei Ogiwara, *Norio Sakai

60

Formation, Characterization, and Reactivity of Acyl Palladium Complexes in Pd(OAc)2/PCy3-Catalyzed Transformation of Acyl Fluorides

Hiroyuki Hattori, *Yohei Ogiwara, *Norio Sakai

Cover Art (URL)

59

Iodine-promoted C-H sulfidation of electron-deficient fluorine-containing arenes with thiols or diselenides leading to unsymmetrical introduction of sulfide or selenide moieties onto tetrafluorobenzene

*Norio Sakai, Mio Ishii, Shouya Tsukahara, Yohei Ogiwara

58

Synthesis of Dibenzotetrathiafulvalenes of Oxalic Acid with Electron-Rich Aromatic 1,2-Dithiols and Application to Dithioacetalization with 9-Fluorenecarboxylic Acids or Dicarboxylic Acids

*Norio Sakai, Kohei Minato, Shota Nakata, Yohei Ogiwara

57

Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction

Takumi Nakajima, Ken Takano, Hiromu Maeda, Yohei Ogiwara, *Norio Sakai

56

Palladium-Catalyzed Intramolecular Aromatic C–H Acylation of 2-Arylbenzoyl Fluorides

Yuka Sakurai, Kana Ikai, Kazuki Hayakawa, *Yohei Ogiwara, *Norio Sakai

55

Indium-Catalyzed Deoxygenation of Sulfoxides with Hydrosilanes

*Norio Sakai, Retsu Shimada, Yohei Ogiwara

54

Palladium-Catalyzed [5 + 1] Annulation of Salicylic Acid Derivatives and Propargylic Carbonates

Kazuya Sato, *Yohei Ogiwara, *Norio Sakai

53

Palladium-Catalyzed Annulation of Acyl Fluorides with Norbornene via Decarbonylation and CO Reinsertion

Yuka Sakurai, *Yohei Ogiwara, *Norio Sakai

Cover Picture (10.1002/chem.202003335)

52

One-Pot Synthesis of α-Halo β-Amino Acid Derivatives via the Difunctional Coupling of Ethyl α-Diazoacetate with Silyl Halides and N,O-Acetals or Aromatic Tertiary Amines

*Norio Sakai, Kazuki Sasaki, Hiroki Suzuki, Yohei Ogiwara

51

Benzoyl Fluorides as Fluorination Reagents: Reconstruction of Acyl Fluorides via Reversible Acyl C–F Bond Cleavage/Formation in Palladium Catalysis

*Yohei Ogiwara, Shintaro Hosaka, *Norio Sakai

Cover Art (URL)

Press Release (English, Japanese) EurekAlert! (URL)

Virtual Issue: Fluorine: A Very Special Element and Its Very Special Impacts on Chemistry (10.1021/acs.inorgchem.1c03509)

Wikipedia (Japanese)

50

One-Pot Synthesis of Dithioacetals and Diselenoacetals: An Indium-Catalyzed Reductive Insertion into Disulfides and Diselenides with Orthoesters as a Methylene Source

*Norio Sakai, Shunpei Adachi, Sho Ogawa, Kenshiro Takahashi, Yohei Ogiwara

Cover Picture (10.1002/ajoc.202000053)

49

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

*Yohei Ogiwara, Yurika Iino, *Norio Sakai

48

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

*Norio Sakai, Hiromu Maeda, Yohei Ogiwara

47

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

Kota Nishino, Shouya Tsukahara, Yohei Ogiwara, *Norio Sakai

46

Construction of N-Heterocyclic Systems Containing a Fully Substituted Allylic Carbon by Palladium/Phosphine Catalysis

*Yohei Ogiwara, Yui Suzuki, Kazuya Sato, *Norio Sakai

45

Group 4 Metallocene Difluoride/Palladium Bimetallic Catalysts for the Reductive Cross-Coupling of Alkynes with Aryl Iodides and Bromides

Keita Takahashi, Hiromitsu Morishita, Yohei Ogiwara, *Norio Sakai

44

Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

*Yohei Ogiwara, Yuka Sakurai, Hiroyuki Hattori, *Norio Sakai

43

Palladium(II)-Catalyzed Synthesis of Dibenzothiophenes from 2-Biphenylyl Disulfides by C–H Functionalization

Kota Nishino, Yohei Ogiwara, *Norio Sakai

42

Indium-Catalyzed Direct Conversion of Lactones into Thiolactones Using a Disilathiane as a Sulfur Source

Yohei Ogiwara, Ken Takano, Shuhei Horikawa, *Norio Sakai

41

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

*Norio Sakai, Koji Takada, Masahiro Katayama, Yohei Ogiwara

40

Palladium‐Catalyzed Reductive Coupling Reaction of Terminal Alkynes with Aryl Iodides Utilizing Hafnocene Difluoride as a Hafnium Hydride Precursor Leading to trans‐Alkenes

Keita Takahashi, Yohei Ogiwara, *Norio Sakai

39

Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium

*Norio Sakai, Shuhei Horikawa, Yohei Ogiwara

38

Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane

Yohei Ogiwara, Hiromu Maeda, *Norio Sakai

Thieme Chemistry News-Archive 2017 (URL)

37

One-pot two-step conversion of aromatic carboxylic acids and esters to aromatic aldehydes via indium-catalyzed reductive thioacetalization and desulfurization

*Norio Sakai, Kohei Minato, Yohei Ogiwara

36

Copper-catalyzed Cyanation of Aryl Iodides Using Nitromethane

Yohei Ogiwara, Hiromitsu Morishita, Minoru Sasaki, Hiroki Imai, *Norio Sakai

35

Palladium-Catalyzed Cyclization of Alkynoic Acids To Form Vinyl Dioxanones Bearing a Quaternary Allylic Carbon

*Yohei Ogiwara, Kazuya Sato, *Norio Sakai

34

Green Preparation of Dibenzothiophene Derivatives Using 2-Biphenylyl Disulfides in the Presence of Molecular Iodine and Its Application to Dibenzoselenophene Synthesis

Kota Nishino, Yohei Ogiwara, *Norio Sakai

33

Acid Fluorides as Acyl Electrophiles in Suzuki–Miyaura Coupling

*Yohei Ogiwara, Daisuke Sakino, Yuka Sakurai, *Norio Sakai

32

Carboxamides as N-Alkylating Reagents of Secondary Amines in Indium-Catalyzed Reductive Amination with a Hydrosilane

Yohei Ogiwara, Wataru Shimoda, Keisuke Ide, Takumi Nakajima, *Norio Sakai

Front Cover (10.1002/ejoc.201700684)

31

Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization

Kota Nishino, Kohei Minato, Takahiro Miyazaki, Yohei Ogiwara, *Norio Sakai

30

Cobalt(II)-Catalyzed Oxidative Coupling of Aromatic Tertiary Amines with Enol Silyl Ethers Leading to β-Aminoketone Derivatives

*Norio Sakai, Takuya Muraoka, Shun Matsumoto, Akihiro Mutsuro, Yohei Ogiwara

29

Indium-catalyzed Reduction of a Nitroarene Using a Hydrosilane: A Selective Reduction Strategy for the Efficient Synthesis of Indoprofen

Yohei Ogiwara, Yuka Sakurai, *Norio Sakai

28

Syntheses of RuHCl(CO)(PAr3)3 and RuH2(CO)(PAr3)3 Containing Various Triarylphosphines and Their Use for Arylation of Sterically Congested Aromatic C–H Bonds

Yohei Ogiwara, Masashi Miyake, Takuya Kochi, *Fumitoshi Kakiuchi

27

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

*Norio Sakai, Hiroki Suzuki, Hiroaki Hori, Yohei Ogiwara

26

Indium(III) Isopropoxide as a Hydrogen Transfer Catalyst for Conversion of Benzylic Alcohols into Aldehydes or Ketones via Oppenauer Oxidation

Yohei Ogiwara, Yuji Ono, *Norio Sakai

25

Cobalt-catalyzed oxidative annulation of aromatic tertiary amines with electron-deficient maleimides leading to tetrahydroquinoline derivatives

*Norio Sakai, Shun Matsumoto, Yohei Ogiwara

24

Gallium-catalyzed reductive lactonization of γ-keto acids with a hydrosilane

*Norio Sakai, Shuhei Horikawa, Yohei Ogiwara

23

Palladium-catalyzed Coupling of Benzoyl Halides with Aryltrifluorosilanes Leading to Diaryl Ketones

Yohei Ogiwara, Yuki Maegawa, Daisuke Sakino, *Norio Sakai

22

Indium-catalyzed reductive three-component coupling reaction of aliphatic/aromatic carboxylic acids with t-butyl mercaptan leading to unsymmetrical dialkyl sulfides

*Norio Sakai, Shunsuke Yoshimoto, Takahiro Miyazaki, Yohei Ogiwara

21

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

*Norio Sakai, Kota Enomoto, Mitsumasa Takayanagi, Takeo Konakahara, Yohei Ogiwara

20

Production of Quaternary α-Aminonitriles by Means of Indium-Catalyzed Three-Component Reaction of Alkynes, Amines, and Trimethylsilyl Cyanide

Yuta Hamachi, Moe Katano, Yohei Ogiwara, *Norio Sakai

19

Indium-Catalyzed Reductive Sulfid­ation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides

Takahiro Miyazaki, Shinsei Kasai, Yohei Ogiwara, *Norio Sakai

18

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

Takahiro Miyazaki, Masahiro Katayama, Shunsuke Yoshimoto, Yohei Ogiwara, *Norio Sakai

17

Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst

Yohei Ogiwara, Takuya Uchiyama, *Norio Sakai

16

Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using Indium(III) Bromide

Yohei Ogiwara, Masahito Kubota, Kotaro Kurogi, Takeo Konakahara, *Norio Sakai

Synfacts (10.1055/s-0035-1561146)

15

One-pot Synthesis of Tetralin Derivatives from 3-Benzoylpropionic Acids: Indium-catalyzed Hydrosilylation of Ketones and Carboxylic Acids and Intramolecular Cyclization

*Norio Sakai, Taichi Kobayashi, Yohei Ogiwara

14

Indium-catalyzed reduction of secondary amides with a hydrosiloxane leading to secondary amines

*Norio Sakai, Masashi Takeoka, Takayuki Kumaki, Hirotaka Asano, Takeo Konakahara, Yohei Ogiwara

13

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

*Norio Sakai, Shun Asama, Takeo Konakahara, Yohei Ogiwara

12

Copper(II)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere

*Norio Sakai, Minoru Sasaki, Yohei Ogiwara

11

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

*Norio Sakai, Hiroaki Hori, Yoshihiro Yoshida, Takeo Konakahara, Yohei Ogiwara

10

Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

Yohei Ogiwara, Keita Takahashi, Takefumi Kitazawa, *Norio Sakai

9

Indium(III)-Catalyzed Reductive Monoalkylation of Electron-Rich Benzenes with Aliphatic Carboxylic Acids Leading to Arylalkane Derivatives

Toshimitsu Moriya, Kentaro Takayama, Takeo Konakahara, Yohei Ogiwara, *Norio Sakai

8

Copper(II)-Catalyzed [4+1] Annulation of Propargylamines with N, O-Acetals: Entry to the Synthesis of Polysubstituted Pyrrole Derivatives

*Norio Sakai, Hiroaki Hori, Yohei Ogiwara

7

Indium-Catalyzed Reductive Sulfidation of Aromatic Carboxylic Acids and Aldehydes with Elemental Sulfur to Prepare Symmetrical Benzyl Sulfides

Takahiro Miyazaki, Kota Nishino, Shunsuke Yoshimoto, Yohei Ogiwara, *Norio Sakai

6

One-Pot Preparation of Alkyl Iodides from Esters by Indium-Catalyzed Reductive Cleavage of a Carbon–Oxygen Bond

*Norio Sakai, Yohei Matsushita, Takeo Konakahara, Yohei Ogiwara, Keisuke Hirano

5

Gallium-Catalyzed Reductive Chlorination of Carboxylic Acids with Copper(II) Chloride

*Norio Sakai, Takumi Nakajima, Shinichiro Yoneda, Takeo Konakahara, Yohei Ogiwara

4

Indium-Catalyzed Hydroamination/Hydrosilylation of Terminal Alkynes and Aromatic Amines through a One-Pot, Two-Step Protocol

*Norio Sakai, Nobuaki Takahashi, Yohei Ogiwara

3

Ruthenium-catalyzed Ortho-selective Aromatic C–H Alkenylation with Alkenyl Carbonates

Yohei Ogiwara, Takuya Kochi, *Fumitoshi Kakiuchi

2

Ruthenium-Catalyzed Ortho-Selective C–H Alkenylation of Aromatic Compounds with Alkenyl Esters and Ethers

Yohei Ogiwara, Masaru Tamura, Takuya Kochi, Yusuke Matsuura, Naoto Chatani, *Fumitoshi Kakiuchi

1

Ruthenium-Catalyzed Conversion of sp3 C–O Bonds in Ethers to C–C Bonds Using Triarylboroxines

Yohei Ogiwara, *Takuya Kochi, *Fumitoshi Kakiuchi

Reviews & Accounts / 総説

4

フッ化アシルを利用した分子変換反応に関する最近の動向

Recent Advances in Transformation of Acyl Fluorides

桜井優香, *荻原陽平, *坂井教郎

Yuka Sakurai, *Yohei Ogiwara, *Norio Sakai

3

Acyl Fluorides in Late-Transition-Metal Catalysis

*Yohei Ogiwara, *Norio Sakai

Carbonsäurefluoride in der Katalyse durch späte Übergangsmetalle

Angew. Chem. 2020, 132, 584−605.

2

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 Transformations Using Hydrosilanes

荻原陽平, *坂井教郎

Yohei Ogiwara, *Norio Sakai

1

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

Reductive Elimination of sp2 Carbon–Halogen Bonds from Palladium (II) Centers: Recent Developments

荻原陽平

Yohei Ogiwara

Book, Highlights, etc. / 著書・解説・その他

5

岐阜大学着任に際しての抱負

荻原陽平

4

元気先生がゆく(インタビュー記事)

荻原陽平

3

カルコゲン結合を利用した触媒反応 −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

2

国際会議 ICOMC 2018

荻原陽平

1

有機フッ素化合物の新しい合成法の開発を目指して

荻原陽平, 坂井教郎