928256-40-0

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 347885-68-1 4-bromo-1-tosylpiperidine 
• 696-62-8 para-iodoanisole 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 147636-36-0 1-[(4-methylphenyl)sulfonyl]piperidine-4-carboxylic acid 
• 97302-05-1 di-4-methoxyphenylzinc 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 80213-12-3 1-[(4-methylbenzene)-sulfonyl]-4-piperidinol 
• 98-59-9 p-toluenesulfonyl chloride 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Downstream Products

• 886198-39-6 C₁₈H₁₉NO₅S 
• 886198-32-9 4-(4-methoxy-phenyl)-1-(toluene-4-sulfonyl)-piperidine-3,4-diol 

Relevant academic research and scientific papers

Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides

Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

Modular radical cross-coupling with sulfones enables access to sp3-rich (fluoro)alkylated scaffolds

Cross-coupling chemistry is widely applied to carbon-carbon bond formation in the synthesis of medicines, agrochemicals, and other functional materials. Recently, single-electron-induced variants of this reaction class have proven particularly useful in the formation of C(sp2)-C(sp3) linkages, although certain compound classes have remained a challenge. Here, we report the use of sulfones to activate the alkyl coupling partner in nickel-catalyzed radical cross-coupling with aryl zinc reagents. This method's tolerance of fluoroalkyl substituents proved particularly advantageous for the streamlined preparation of pharmaceutically oriented fluorinated scaffolds that previously required multiple steps, toxic reagents, and nonmodular retrosynthetic blueprints. Five specific sulfone reagents facilitate the rapid assembly of a vast set of compounds, many of which contain challenging fluorination patterns.

Nickel-catalyzed reductive coupling of aryl halides with secondary alkyl bromides and allylic acetate

A room-temperature Ni-catalyzed reductive method for the coupling of aryl bromides with secondary alkyl bromides has been developed, providing C(sp 2)-C(sp3) products in good to excellent yields. Slight modification of this protocol allows efficient coupling of activated aryl chlorides with cyclohexyl bromide and aryl bromides with allylic acetate.

CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines

A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to β-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5).