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Issue 62, 2016
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Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive N-alkylation of secondary amines with ketones through an alternative pathway

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Abstract

We report herein a highly efficient, tin(II)/PMHS catalyzed reductive N-alkylation of arylamines with ketones affording tertiary arylamines. A very wide substrate scope was observed for the current catalytic method as all six permutations of ketones/aldehydes/heterocyclic carbonyls and primary/secondary/heterocyclic amines were well tolerated, enabling access to secondary, tertiary and heterocyclic amines. The method is also convenient for the synthesis of N-substituted isoindolinones and phthalazinones via a tandem amination–amidation sequence. Mechanistic investigations revealed a carbocationic pathway instead of an ordinary direct reductive amination pathway.

Graphical abstract: Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive N-alkylation of secondary amines with ketones through an alternative pathway

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Article information


Submitted
25 May 2016
Accepted
21 Jun 2016
First published
22 Jun 2016

Chem. Commun., 2016,52, 9648-9651
Article type
Communication

Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive N-alkylation of secondary amines with ketones through an alternative pathway

O. S. Nayal, M. S. Thakur, V. Bhatt, M. Kumar, N. Kumar, B. Singh and U. Sharma, Chem. Commun., 2016, 52, 9648
DOI: 10.1039/C6CC04381J

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