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• W2600283444 startingPage "5178" @default.
• W2600283444 abstract "Treatment of N-substituted pyrroles with carbonyl compounds and nucleophiles under indium catalysis was found to be a promising method for preparing β-alkylpyrroles without contamination by α-alkylpyrroles. With this methodology, a variety of alkyl groups, which are primary, secondary, and tertiary as well as cyclic and functionalized types, can be introduced in place onto the pyrrole ring. The simplicity performable as a catalytic one-step process is one of the important features of this reaction. The substituent on the nitrogen atom of the product β-alkylpyrrole can be removed easily by literature procedures. Therefore, the indium-catalyzed β-alkylation plus the N-deprotection is a powerful system for all six variations, which are N-substituted and N-unsubstituted β-alkylpyrroles having primary, secondary, and tertiary alkyl groups. Our method is applicable to synthesizing, albeit in two steps, β-pyrrolyl-group-connected unsymmetrical tetraarylmethanes that have not been addressed thus far. Mechanistic studies showed the following three aspects: (1) dipyrrolylalkanes produced in situ from the pyrrole and carbonyl compound are key intermediates, (2) the selective β-alkylation is attributed to the selective elimination of an α-pyrrolyl group from the dipyrrolylalkane intermediates, and (3) the indium Lewis acid catalyst is indispensable for the progress of both stages." @default.
• W2600283444 created "2017-04-07" @default.
• W2600283444 creator A5026334591 @default.
• W2600283444 creator A5059952361 @default.
• W2600283444 creator A5061871146 @default.
• W2600283444 creator A5066940666 @default.
• W2600283444 creator A5091288383 @default.
• W2600283444 date "2017-05-05" @default.
• W2600283444 modified "2023-10-18" @default.
• W2600283444 title "Indium-Catalyzed Regioselective β-Alkylation of Pyrroles with Carbonyl Compounds and Hydrosilanes and Its Application to Construction of a Quaternary Carbon Center with a β-Pyrrolyl Group" @default.
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