Visible-Light-Enabled Direct Decarboxylative N-Alkylation |
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Authors: | Vu T Nguyen Viet D Nguyen Graham C Haug Ngan T H Vuong Hang T Dang Dr Hadi D Arman Dr Oleg V Larionov |
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Institution: | 1. Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249 USA
These authors contributed equally to this work.;2. Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249 USA |
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Abstract: | The development of efficient and selective C−N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction. |
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Keywords: | Aminierung Carbonsäuren Kupferkatalyse Photokatalyse Sichtbares Licht |
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