289890-80-8

Upstream product

• 5382-16-1 4-HYDROXYPIPERIDINE 
• 98-59-9 p-toluenesulfonyl chloride 
• 80213-12-3 1-[(4-methylbenzene)-sulfonyl]-4-piperidinol 
• 41979-39-9 4-piperidone hydrochloride 
• 50-00-0 formaldehyd 
• 10285-80-0 N-tosyl-3-butenylamine 
• 101767-94-6 1-<(4-methylphenyl)sulfonyl>-4-piperidinol 4-methylbenzenesulfonate ester 

Downstream Products

• 93431-41-5 1-(4-toluenesulfonyl)-piperidine-4-carbonitrile 
• 1380434-19-4 2,2-dimethyl-1-(1-tosylpiperidin-4-yl)propan-1-one 
• 1380434-23-0 (3-methoxyphenyl)(1-tosylpiperidin-4-yl)methanone 
• 922504-26-5 phenyl(1-tosylpiperidin-4-yl)methanone 
• 604759-84-4 p-tolyl(1-tosylpiperidin-4-yl)methanone 
• 1380434-21-8 o-tolyl(1-tosylpiperidin-4-yl)methanone 
• 1380434-18-3 (4-(tert-butyl)phenyl)(1-tosylpiperidin-4-yl)methanone 
• 143632-57-9 N-(toluenesulfonyl)-4-phenylpiperidine 
• 1274845-59-8 1-(1-p-toluenesulfonylpiperidin-4-yl)ethan-1-one 
• 93148-69-7 4-(2-methylprop-1-en-1-yl)-1-tosylpiperidine 
• 1373334-63-4 4-allyl-1-tosylpiperidine 

Relevant academic research and scientific papers

Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids

Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an inexpensive palladium catalyst to generate the key alkyl radical intermediate. These mild conditions enabled the synthesis of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone.

Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl3-Catalyzed Prins Reaction

A general and practical method for the preparation of trans-2-substituted-4-halopiperidines and cis-2-substituted-4-halotetrahydropyrans is reported. Using 5 mol % of AlCl3 as the catalyst and 2 equiv of trimethylsilyl halides as the halide sou

Triphenylphosphine-Catalyzed Alkylative Iododecarboxylation with Lithium Iodide under Visible Light

Under irradiation of 456 nm blue light-emitting diodes, PPh3 catalyzes the iododecarboxylation of aliphatic carboxylic acid derived N-(acyloxy)phthalimide with lithium iodide as an iodine source. The reaction delivers primary, secondary, and bridgehead te

Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

Radical Deuteration with D2O: Catalysis and Mechanistic Insights

Selective incorporation of deuterium atoms into molecules is of high interest for labeling purposes and for optimizing properties of drug candidates. A mild and environmentally benign method for the deuteration of alkyl iodides via radical pathway using D2O as source of deuterium has been developed. The reaction is initiated and mediated by triethylborane in the presence of dodecanethiol as a catalyst. This method is compatible with a wide range of functional groups and provides the monodeuterated products in good yields and with a high level of deuterium incorporation. It opens promising opportunities for the development of enantioselective radical reactions. Moreover, a revision of the mechanism of the deoxygenation reaction of xanthates using R3B and water (Wood deoxygenation) is presented.

Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni's Reagent

This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl-CF3 products with excellent functional group tolerance and broad substrate scope. A mechanism involving a reaction of alkyl-Cu with Togni's reagent was proposed.

A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones

A convergent synthesis of trifluoromethyl ketones and α,β-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the α- and β-fragmentations of a sulfonyl radical. The transfo

Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents

A cobalt-catalyzed cross-coupling between 3- and 4-iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)-preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates. Scaffold synthesis: A cobalt-catalyzed cross-coupling between iodopiperidines and Grignard reagents is reported (see scheme; PG=protecting group). A large variety of 3- and 4-substituted piperidines were synthesized and the method was applied to a short synthesis of (±)-preclamol. This work constitutes one of the rare examples of cross-couplings involving 3-halogeno piperidines.

Palladium-catalyzed heck-type cross-couplings of unactivated alkyl iodides

A palladium-catalyzed, intermolecular Heck-type coupling of alkyl iodides and alkenes is described. This process is successful with a variety of primary and secondary unactivated alkyl iodides as reaction partners, including those with hydrogen atoms in t

Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with grignard reagents

Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.