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Upstream product

• 39098-97-0 2-thienylacetic acid chloride 
• 882-33-7 diphenyldisulfane 
• 636-72-6 2-thiophenemethanol 
• 108-98-5 thiophenol 
• 13679-77-1 (thiophen-2-yl)methyl acetate 
• 4551-15-9 phenylthiotrimethylsilane 
• 26019-17-0 2-(dimethylaminomethyl)thiophene 
• 1918-77-0 Thiophene-2-acetic acid 
• 63521-93-7 2-(thiophene-2-yl)acetic anhydride 

Relevant academic research and scientific papers

Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates

A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility. This journal is

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is

Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols

Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.

Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction

An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal-free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2-diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions. (Figure presented.).

Synthesis of a wide range of thioethers by indium triiodide catalyzed direct coupling between alkyl acetates and thiosilanes

An indium triiodide-catalyzed substitution of the acetoxy group in alkyl acetates with thiosilanes provides access to a variety of thioethers. The method is efficient for a wide scope of acetates such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic acetates.

Iodine-mediated thioetherification of alcohols with disulfides or NaSh under microwave irradiation

An efficient and novel method for the thioetherification of an alcohol with disulfides or NaSH under microwave irradiation is presented. In the presence of iodine, a variety of alcohols were smoothly S-alkylated with disulfides or NaSH to give the corresponding thioethers in moderate to excellent yields. Copyright

Cobalt-mediated Reactions in Synthesis. The Degradation of Carboxylic Acids to Functionalised Noralkanes via Acylcobalt Salophen Intermediates

Arylmethyl- and allyl-carbonylcobalt salophen complexes, e.g. (7), (8), (9), and (22), readily undergo carbon-to-cobalt-bond homolysis and in situ decarbonylation, producing new alkyl radical centres which can be intercepted with oxygen-, nitrogen-, halogen-, sulphur-, and selenium-containing trapping agents leading to functionalised noralkanes.The sequence constitutes a useful, and in some cases more flexible, variant of the classical Hunsdiecker reaction, and amounts to a cobalt equivalent of the Barton radical decarboxylation reaction of carboxylic acids via their corresponding thiohydroxamic esters.In a similar manner, irradiation of the oxy-substituted acylcobalt salen reagents (25) and (26) in the presence of tetramethylpiperidine oxide produces the products (14) and (27), respectively, resulting from homolysis-decarboxylation and alkyl-radical trapping.In the absence of radical-trapping agents, irradiation of (7c) produces (18), and irradiation of (29) leads to the but-2-enolide (32).

FREE RADICAL REACTIONS INITIATED BY ORGANOCOBALT COMPLEXES. A NEW METHOD FOR THE DEGRADATION OF CARBOXYLIC ACIDS TO FUNCTIONALISED NOR-ALKANES VIA ACYLCOBALT SALOPHEN INTERMEDIATES.

Arylmethyl- and allyl-acylcobalt salophens, undergo facile C-Co bond homolysis and in situ decarbonylation, producing new (alkyl) radical centres which can be intercepted with oxygen, nitrogen, halogen, sulphur and selenium containing radical trapping agents, leading to functionalised nor-alkanes (Scheme).