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.
Circuitos sintéticos 1
1.1
Reagents:
Hydrogen
Catalysts:
Ruthenium
(supported on TiO2)
Solvents:
1,4-Dioxane
;
1 h, 1 atm, 100 °C
Referencia
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
Circuitos sintéticos 2
1.1
Reagents:
Triethylamine
,
Hydrogen
Catalysts:
Chitosan
Solvents:
Methanol
,
Water
;
48 h, 30 bar, 120 °C
Referencia
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
Circuitos sintéticos 3
1.1
Catalysts:
Palladium chloride
Solvents:
Water
;
2 min, rt
1.2
Reagents:
1,1,3,3-Tetramethyldisiloxane
;
rt; rt
Referencia
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
Circuitos sintéticos 4
1.1
Solvents:
Dimethylformamide
;
1 h, 130 °C
Referencia
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
Circuitos sintéticos 5
1.1
Reagents:
Triethylamine
,
Hydrogen
Catalysts:
Nickel
Solvents:
Methanol
,
Water
;
5 - 10 bar; 20 h, 20 - 30 bar, 45 - 130 °C
Referencia
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),
Circuitos sintéticos 6
1.1
Reagents:
N,N,N′,N′-Tetramethylethylenediamine
,
Sodium borohydride
Catalysts:
[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents:
Tetrahydrofuran
;
0.5 h, rt
Referencia
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
Circuitos sintéticos 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
Referencia
Gold(I)-Catalyzed Protodecarboxylation of (Hetero)Aromatic Carboxylic Acids
Dupuy, Stephanie;
Nolan, Steven P.,
Chemistry - A European Journal,
2013,
19(42),
14034-14038
Circuitos sintéticos 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
Referencia
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
Circuitos sintéticos 9
1.1
Reagents:
Tetrabutylammonium bromide
Catalysts:
Nickel alloy, base, Ni 95,Ag 5
Solvents:
Water
;
10 h, 60 °C
Referencia
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
Circuitos sintéticos 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
Referencia
Cobalt-Catalyzed Protodeboronation of Aryl and Vinyl Boronates
Li, Ninglin;
Xiong, Fuqiang;
Gao, Ke,
Journal of Organic Chemistry,
2021,
86(2),
1972-1979
Circuitos sintéticos 11
1.1
Catalysts:
Quinoline
,
Copper
Referencia
Preparation of benzo[b]thiophenes from benzo[b]thiophene-2-carboxylic acids
,
Japan,
,
,
Circuitos sintéticos 12
1.1
Reagents:
Water
Catalysts:
[1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamidato-κN](triphenyl…
Solvents:
Dimethyl carbonate
;
1 h, 90 °C
Referencia
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
Circuitos sintéticos 13
1.1
Solvents:
Dichloromethane
Referencia
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
Circuitos sintéticos 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
Referencia
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
Circuitos sintéticos 15
1.1
Reagents:
Potassium hydroxide
Solvents:
Dimethyl sulfoxide
;
26 h, 25 °C
1.2
Reagents:
Hydrochloric acid
Solvents:
Water
Referencia
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
Circuitos sintéticos 16
1.1
Reagents:
Hydrogen
Catalysts:
Ruthenium
,
Titania
Solvents:
1,4-Dioxane
;
1 h, 1 atm, 100 °C
Referencia
Catalyst for deoxidization of sulfoxide, and method for manufacturing sulfide using catalyst for deoxidization
,
Japan,
,
,
Circuitos sintéticos 17
Referencia
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
Circuitos sintéticos 18
1.1
Reagents:
Oxygen
Catalysts:
Palladium
Solvents:
Cyclohexane
;
24 h, 130 °C
Referencia
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
Circuitos sintéticos 19
1.1
Reagents:
Hydrogen
,
Ammonia
Catalysts:
Palladium
,
Copper
,
Titania
Solvents:
Toluene
;
rt → 250 °C; 4 h, 0.5 MPa, 250 °C
Referencia
A novel synthesis of benzo[b]thiophene
Liao, Zutai;
Lv, Xuehao;
Tao, Ming,
Research on Chemical Intermediates,
2013,
39(9),
4021-4024