51218-06-5Relevant academic research and scientific papers
A novel α-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations
Fraboni, Andrea,Fagnoni, Maurizio,Albini, Angelo
, p. 4886 - 4893 (2003)
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 α-(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 α-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 α-(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 β-methoxy enone. The method is complementary to the recently developed palladium-catalyzed α-arylation and occurs under neutral conditions.
Remarkable catalytic effect of H+ in Michael-type additions of anilines to 3-butyn-2-one
Um, Ik-Hwan,Lee, Eun-Ju,Min, Ji-Sook
, p. 9585 - 9589 (2007/10/03)
Second-order rate constants (kN) for the Michael-type reaction of 3-butyn-2-one (1) with a series of anilines in H2O have been determined spectrophotometrically. The kN values are dependent on the free aniline fraction (F
