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Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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TRANSITION METAL-CATALYZED IMIDATION OF ARENES

The present invention provides novel transition metal complexes (e.g., complexes of any one of Formulae (C1) to (C25)) that include an amine-N-oxide motif. The invention also provides methods of using these transition metal complexes in preparing N-aryl or N- heteroaryl sulfonimides (e.g., compounds of Formula (I)) and aryl or heteroaryl amines (e.g., compounds of Formula (II)). The inventive methods involve imidation of arenes and heteroarenes (e.g., compounds of Formula (A)) using an imidating agent (e.g., a compound of Formula (B), such as N-fluorobenzenesulfonimide (NFBS or NFSI)) in the presence of a single-electron reductant (e.g., an Ag(I) or Ru(II) salt).

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Palladium-catalyzed domino C-S coupling/carbonylation reactions: An efficient synthesis of 2-carbonylbenzo[ b ]thiophene derivatives

A facile and selective palladium-catalyzed domino procedure has been developed for the preparation of 2-carbonylbenzo[b]thiophene derivatives from 2-gem-dihalovinylthiophenols. This protocol involves intramolecular C-S coupling/intermolecular carbonylation cascade sequences and allows access to various highly functionalized benzo[b]thiophenes in moderate yields.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Copper-Catalyzed C2 and C3 Phosphonation of Benzofuran and Benzothiophene with Trialkyl Phosphites

A strategy for the selective phosphonation of benzofuran and benzothiophene with trialkyl phosphites was developed. In these reactions, the C?H phosphonation of benzofurans or benzothiophenes at the C2 or C3 position with trialkyl phosphites was successfully achieved without directing groups by using a copper catalyst. Additionally, the C5 phosphonation of furan was successful under the same conditions.

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In situ generated “lanthanum(iii) nitrate alkoxide” as a highly active and nearly neutral transesterification catalyst

In situ generated lanthanum(iii) nitrate alkoxide is a highly active and nearly neutral transesterification catalyst, which can promote non-epimerized transesterification of alpha-substituted chiral carboxylic esters under reflux conditions.

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Benzothiophene – Wikipedia,
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Imidazolyl-substituted benzothiophenes

The present invention provides novel imidazolyl-benzothiophenes and derivatives thereof which are useful as thromboxane A2 (TXA2) synthetase inhibitors and as such represent potent pharmacological agents.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Telomerase inhibitors

Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds characterized by the following structure: STR1 and their pharmaceutically acceptable salts. Y is selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, and –NR7 –. R1 is –TR8, where T is –C(X1)– or –SO2 –, and R8 is selected from the group consisting of –OR9, –NHNHSO2 R9, –NHNHC(X2)OR9, –NR9 R10, –NHNHC(X2)NR9 R10, –NHCR9 R10 C(X2)NR11 R12, –NHC(X2)NR9 R10, and the piperazinyl moiety shown below: STR2 where n is 0 or 1, and Qn, for n=1, is –SO2 –, –C(X2)– or –C(X2)NR10 –. R2 -R6 are selected independently from the group consisting of hydrogen, alkyl, aryl, hydroxyl, alkoxyl, aryloxyl, aralkoxyl, halogen, cyano, nitro, alkylcarbamido, arylcarbamido, dialkylcarbamido, diarylcarbamido, alkylarylcarbamido, alkylthiocarbamido, arylthiocarbamido, dialkylthiocarbamido, diarylthiocarbamido, alkylarylthiocarbamido, amino, alkylamino, arylamino, dialkylamino, diarylamino, arylalkylamino, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, arylalkylaminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, carboxyl, alkoxycarbonyl, aryloxycarbonyl, sulfo, alkylsulfonylamido, arylsulfonylamido, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, and arylsulfinyl. X1 and X2 are selected independently from the group consisting of oxygen, and sulfur. R7 -R12 are selected independently from the group consisting of hydrogen, alkyl, aryl, aralkyl, heterocycle, and heterocyclealkyl.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Transition-Metal-Free Synthesis of C3-Arylated Benzofurans from Benzothiophenes and Phenols

We report a transition-metal-free synthesis of benzofurans from benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Through a sequence involving an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement, phenols can be combined with readily accessible yet synthetically unexplored benzothiophene S-oxides to provide C3-arylated benzofuran products. The products from this approach can undergo subsequent functionalization to gain access to a range of important benzofuran derivatives.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthesis and electrochemical reduction of methyl 3-halo-1-benzothiophene- 2-carboxylates

A preparative method of synthesis of the new methyl 3-iodo-1- benzothiophene-2-carboxylate was elaborated. Electrochemical behavior of methyl 3-chloro-, bromo- and iodo-1-benzothiophene-2-carboxylates 1-3, and of their reduction and dimer products 4, 5 in anhydrous dimethylformamide has been investigated at mercury and platinum electrodes using polarography, cyclic voltammetry and voltammetry on a rotating platinum disk electrode. The reduction in divided cells follows the ECE mechanism (electron – chemical step – electron), where the primary radical anion is split into a halide anion and neutral heterocyclic radical, which is immediately reduced by the second electron and protonated. The only reduction product is the methyl 1-benzothiophene-2-carboxylate (5); whereas the EDim mechanism (electron – dimer formation) leading to the dimeric species 4 was not observed under the above conditions. Reduction of 1-3 on platinum causes formation of a blocking film on the electrode. Sonication during electrolysis successfully reactivates the electrode.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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sigma-Bond initiated generation of aryl radicals from aryl diazonium salts

sigma-Bond nucleophiles and molecular oxygen transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been illustrated in a variety of bond-forming reactions.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem