Benzothiophene(Thianaphthene)It's an organic chemical,The molecular formula isC8H6S,White foliar crystals.Naphthalene like smell.Industrially Mainly extracted from crude naphthalene.Also available
styrene or
ethylbenzeneSynthesized with hydrogen sulfide or synthesized from
thiophenePrepared by condensation with benzene ring.Mainly used in the manufacture of drugs and thioindigo.
Circuito sintetico 1
1.1
Reagents:
Hydrogen
Catalysts:
Ruthenium
(supported on TiO2)
Solvents:
1,4-Dioxane
;
1 h, 1 atm, 100 °C
Riferimento
Hydrogenation of sulfoxides to sulfides under mild conditions using ruthenium nanoparticle catalysts
Mitsudome, Takato;
Takahashi, Yusuke;
Mizugaki, Tomoo;
Jitsukawa, Koichiro;
Kaneda, Kiyotomi,
Angewandte Chemie,
2014,
53(32),
8348-8351
Circuito sintetico 2
1.1
Reagents:
Triethylamine
,
Hydrogen
Catalysts:
Chitosan
Solvents:
Methanol
,
Water
;
48 h, 30 bar, 120 °C
Riferimento
A Biomass-Derived Non-Noble Cobalt Catalyst for Selective Hydrodehalogenation of Alkyl and (Hetero)Aryl Halides
Sahoo, Basudev;
Surkus, Annette-Enrica;
Pohl, Marga-Martina;
Radnik, Joerg;
Schneider, Matthias; et al,
Angewandte Chemie,
2017,
56(37),
11242-11247
Circuito sintetico 3
1.1
Catalysts:
Palladium chloride
Solvents:
Water
;
2 min, rt
1.2
Reagents:
1,1,3,3-Tetramethyldisiloxane
;
rt; rt
Riferimento
Ligand-Free, Palladium-Catalyzed Dihydrogen Generation from TMDS: Dehalogenation of Aryl Halides on Water
Bhattacharjya, Anish;
Klumphu, Piyatida;
Lipshutz, Bruce H.,
Organic Letters,
2015,
17(5),
1122-1125
Circuito sintetico 4
1.1
Solvents:
Dimethylformamide
;
1 h, 130 °C
Riferimento
Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzothiophenes via the Annulation of Aryl Sulfides with Alkynes
Masuya, Yoshihiro;
Tobisu, Mamoru;
Chatani, Naoto,
Organic Letters,
2016,
18(17),
4312-4315
Circuito sintetico 5
1.1
Reagents:
Triethylamine
,
Hydrogen
Catalysts:
Nickel
Solvents:
Methanol
,
Water
;
5 - 10 bar; 20 h, 20 - 30 bar, 45 - 130 °C
Riferimento
A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen
Leonard, David K.
;
Ryabchuk, Pavel
;
Anwar, Muhammad
;
Dastgir, Sarim
;
Junge, Kathrin
; et al,
ChemSusChem,
2022,
15(5),
Circuito sintetico 6
1.1
Reagents:
N,N,N′,N′-Tetramethylethylenediamine
,
Sodium borohydride
Catalysts:
[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents:
Tetrahydrofuran
;
0.5 h, rt
Riferimento
Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms
Chelucci, Giorgio;
Baldino, Salvatore;
Ruiu, Andrea,
Journal of Organic Chemistry,
2012,
77(21),
9921-9925
Circuito sintetico 7
1.1
Catalysts:
[1,3-Bis[2,6-bis(1-methylethyl)phenyl]-2-imidazolidinylidene](tricyclo[3.3.1.13,…
Solvents:
Toluene
;
16 h, 120 °C
Riferimento
Gold(I)-Catalyzed Protodecarboxylation of (Hetero)Aromatic Carboxylic Acids
Dupuy, Stephanie;
Nolan, Steven P.,
Chemistry - A European Journal,
2013,
19(42),
14034-14038
Circuito sintetico 8
1.1
Reagents:
Hydrogen
,
1,8-Diazabicyclo[5.4.0]undec-7-ene
Catalysts:
2511739-39-0
Solvents:
Dimethyl sulfoxide
;
12 h, 1 atm, 80 °C
Riferimento
Radical Hydrodehalogenation of Aryl Halides with H2 Catalyzed by a Phenanthroline-Based PNNP Cobalt(I) Complex
Jheng, Nai-Yuan;
Ishizaka, Yusuke;
Naganawa, Yuki
;
Minami, Yasunori
;
Sekiguchi, Akira; et al,
ACS Catalysis,
2022,
12(4),
2320-2329
Circuito sintetico 9
1.1
Reagents:
Tetrabutylammonium bromide
Catalysts:
Nickel alloy, base, Ni 95,Ag 5
Solvents:
Water
;
10 h, 60 °C
Riferimento
Preparation of a cost-effective Ni-Ag bimetallic catalyst for hydrodehalogenation of aryl halides under mild conditions
Deng, Jiazhu;
Xue, Teng;
Wu, Haihong;
Wu, Peng,
New Journal of Chemistry,
2022,
46(25),
12169-12176
Circuito sintetico 10
1.1
Reagents:
Lithium tert-butoxide
,
Water
Catalysts:
Cobalt dibromide
,
1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1)
Solvents:
Tetrahydrofuran
;
6 h, 80 °C; 80 °C → rt
1.2
Reagents:
Ammonium chloride
Solvents:
Water
;
rt
Riferimento
Cobalt-Catalyzed Protodeboronation of Aryl and Vinyl Boronates
Li, Ninglin;
Xiong, Fuqiang;
Gao, Ke,
Journal of Organic Chemistry,
2021,
86(2),
1972-1979
Circuito sintetico 11
1.1
Catalysts:
Quinoline
,
Copper
Riferimento
Preparation of benzo[b]thiophenes from benzo[b]thiophene-2-carboxylic acids
,
Japan,
,
,
Circuito sintetico 12
1.1
Reagents:
Water
Catalysts:
[1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamidato-κN](triphenyl…
Solvents:
Dimethyl carbonate
;
1 h, 90 °C
Riferimento
Gold-Catalyzed Proto- and Deuterodeboronation
Barker, Graeme;
Webster, Stacey;
Johnson, David G.;
Curley, Rachel;
Andrews, Matthew; et al,
Journal of Organic Chemistry,
2015,
80(20),
9807-9816
Circuito sintetico 13
1.1
Solvents:
Dichloromethane
Riferimento
Photolysis of β-[o-(methylthio)phenyl]vinyl bromides. A versatile synthesis of benzo[b]thiophenes
Kitamura, Tsugio;
Kobayashi, Shinjiro;
Taniguchi, Hiroshi,
Chemistry Letters,
1988,
(10),
1637-8
Circuito sintetico 14
1.1
Reagents:
N,N,N′,N′-Tetramethylethylenediamine
,
Sodium borohydride
Catalysts:
(SP-4-2)-[1,1′-Bis[bis(1,1-dimethylethyl)phosphino-κP]ferrocene]dichloropalladiu…
Solvents:
Tetrahydrofuran
;
8 h, 65 °C
Riferimento
NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
Chelucci, Giorgio;
Figus, Susanna,
Journal of Molecular Catalysis A: Chemical,
2014,
393,
191-209
Circuito sintetico 15
1.1
Reagents:
Potassium hydroxide
Solvents:
Dimethyl sulfoxide
;
26 h, 25 °C
1.2
Reagents:
Hydrochloric acid
Solvents:
Water
Riferimento
Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light
Gao, Li;
Chang, Bin;
Qiu, Wenzhao;
Wang, Lele;
Fu, Xianzhi; et al,
Advanced Synthesis & Catalysis,
2016,
358(8),
1202-1207
Circuito sintetico 16
1.1
Reagents:
Hydrogen
Catalysts:
Ruthenium
,
Titania
Solvents:
1,4-Dioxane
;
1 h, 1 atm, 100 °C
Riferimento
Catalyst for deoxidization of sulfoxide, and method for manufacturing sulfide using catalyst for deoxidization
,
Japan,
,
,
Circuito sintetico 17
Riferimento
High-temperature organic synthesis. XXXI. Reaction of phenylthio radicals with acetylene, phenylacetylene, and propargyl alcohol
Sukhomazova, E. N.;
Russavskaya, N. V.;
Korchevin, N. A.;
Deryagina, E. N.;
Voronkov, M. G.,
Zhurnal Organicheskoi Khimii,
1989,
25(7),
1506-12
Circuito sintetico 18
1.1
Reagents:
Oxygen
Catalysts:
Palladium
Solvents:
Cyclohexane
;
24 h, 130 °C
Riferimento
Fibrous-Silica Supported Palladium-Nanoparticles (KCC-1-PEI/Pd): A Sustainable Nanocatalyst for Decarbonylation Reactions
Kundu, Pintu K.;
Dhiman, Mahak;
Modak, Atanu;
Chowdhury, Arindam;
Polshettiwar, Vivek; et al,
ChemPlusChem,
2016,
81(11),
1142-1146
Circuito sintetico 19
1.1
Reagents:
Hydrogen
,
Ammonia
Catalysts:
Palladium
,
Copper
,
Titania
Solvents:
Toluene
;
rt → 250 °C; 4 h, 0.5 MPa, 250 °C
Riferimento
A novel synthesis of benzo[b]thiophene
Liao, Zutai;
Lv, Xuehao;
Tao, Ming,
Research on Chemical Intermediates,
2013,
39(9),
4021-4024