A novel alpha-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations.

doi:10.1021/JO034375P

Paper

A novel alpha-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations.

Published Jun 13, 2003 · Andrea Fraboni, M. Fagnoni, A. Albini

The Journal of organic chemistry

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37

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Abstract

4-Aminophenyl cations (expediently generated by photolysis of 4-chloroaniline and its N,N-dimethyl derivative by photolysis in MeCN) added to enamines and gave the corresponding alpha-(4-aminophenyl) ketones in satisfactory yields. The yields of the same ketones were increased when silyl enol ethers were used in the place of enamines. The alpha-arylation of silyl enol ethers of aldehydes occurred with lower yields and only with the N,N-dimethyl derivative. The procedure was successful with ketene silyl acetals giving in a single step a good yield of alpha-(4-aminophenyl)propionic(acetic) esters, known intermediates for the preparation of analgesic compounds. The reaction of the aryl cation with Danishefsky's diene gave the arylated beta-methoxy enone. The method is complementary to the recently developed palladium-catalyzed alpha-arylation and occurs under neutral conditions.

Study Snapshot

This study presents a novel alpha-arylation method using 4-aminophenyl cations, which can produce alpha-(4-aminophenyl) ketones, aldehydes, and esters under neutral conditions, potentially benefiting analgesic compound preparation.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

A novel alpha-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations.

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