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A multicomponent synthesis of tetrahydroisoquinolines from carboxylic acids, alkynyl ethers, and dihydroisoquinolines is described. This process features readily available starting materials, simple experimental procedures for achievement of molecule complexity, and structural diversity. The preliminary control experiment and crossover reaction provide important insight into the reaction mechanism. The formed tetrahydroisoquinolines could be transformed to an array of compounds.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H22715N – PubChem

 

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Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H22693N – PubChem

 

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The silver-catalyzed Hunsdiecker bromination of aliphatic carboxylic acids is described. With Ag(Phen)2OTf as the catalyst and dibromoisocyanuric acid as the brominating agent, various aliphatic carboxylic acids underwent decarboxylative bromination to provide the corresponding alkyl bromides under mild conditions. This method not only is efficient and general but also enjoys wide functional group compatibility. An oxidative radical mechanism involving Ag(II) intermediates is proposed.

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Piperidine – Wikipedia,
Piperidine | C5H22677N – PubChem

 

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The invention relates to a novel styrene compound and its prevention of agricultural disease in the application, and in particular relates to a compound of the formula I structure, stereo isomer, tautomer, geometrical isomer or its pharmaceutically acceptable salt, characterized in that states the type I structure is as follows: R1 Is selected from halogen, C1 – C4 alkoxy, C1 – C4 alkyl, halogenated C1 – C4 alkyl; R2 Is selected from H, C1 – C4 alkyl, R3 , R4 Are each independently selected from optionally one or more of Ra Substituted C1 – C4 alkyl, – NHBoc, or R3 And R4 Is optionally substituted with one or more Ra Substituted five to six membered ring alkyl or nitrogen heterocyclic alkyl; or R2 , R3 , R4 Optionally together with one or more C1 – C4 alkyl, C1 – C4 alkoxy, – C (O) ORb Substituted bridge cycloalkane; Rb Selected from C1 – C4 alkyl; n is 0 – 5 integer. (by machine translation)

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H22683N – PubChem

 

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 147636-36-0, molcular formula is C13H17NO4S, introducing its new discovery. name: 1-Tosylpiperidine-4-carboxylic acid

An approach for the synthesis of alpha-aryl alkylphosphonates based on visible-light photocatalytic Giese reaction of alpha-aryl vinylphosphonates with aliphatic carboxylic acids has been successfully developed. This protocol tolerates a wide range of functional groups and shows broad substrate scope with regard to both the carboxylic acid and vinylphosphonate components. With sequential Giese/hydrolysis reactions as the strategy, the oxo-phosphonates could be easily accessible. The synthetic application of the hydroformylation reaction was demonstrated by the synthesis of the intermediate of alpha-phenyl substituted fosmidomycin analogue. Furthermore, the competitive decarboxylative alkylation of vinylphosphonate and acrylate was also investigated. (Figure presented.).

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Piperidine – Wikipedia,
Piperidine | C5H22707N – PubChem

 

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A novel NiH-catalyzed decarboxylative hydroalkylation of internal alkynes has been developed. Trisubstituted olefins were obtained in moderate to good yields with good regioselectivities. The reaction involves cis addition of NiH to the internal alkyne. The reaction shows good functional-group tolerance.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H22713N – PubChem

 

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An one-pot reaction of carboxylic acids and ynol ethers for the synthesis of beta-keto esters has been developed. Under promotion of Ag2O, various carboxylic acids and ynol ethers could transform to alpha-acyloxy enol esters, which undergo a following DMAP-catalyzed rearrangement to deliver beta-keto esters rapidly. This method provides a direct approach to beta-keto esters from carboxylic acids without any preactivation. The protocol features mild reaction conditions, broad substrate scope, and the products could be transformed to an array of compounds.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H22701N – PubChem

 

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Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification

A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ?40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.

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Piperidine – Wikipedia,
Piperidine | C5H22711N – PubChem

 

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Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis

Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal-catalyzed cross-coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross-coupling of alkyl N-hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone-derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.

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Piperidine – Wikipedia,
Piperidine | C5H22708N – PubChem