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Tunable, chemoselective amination via silver catalysis.

ABSTRACT: Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C-H bond or add it directly to a C?C bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, we report remarkable chemoselective aminations that employ a single metal (Ag) and a single ligand (phenanthroline) to promote either aziridination or C-H insertion by manipulating the coordination geometry of the active catalysts.

SUBMITTER: Rigoli JW

PROVIDER: S-EPMC4492479 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Tunable, chemoselective amination via silver catalysis.

Rigoli Jared W JW Weatherly Cale D CD Alderson Juliet M JM Vo Brian T BT Schomaker Jennifer M JM

Journal of the American Chemical Society 20131111 46

Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C-H bond or add it directly to a C═C bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, ...[more]

PMID: 24187997

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