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Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3 )-H Bonds*.


ABSTRACT: The metal-free activation of C(sp3 )-H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

SUBMITTER: Murugesan K 

PROVIDER: S-EPMC7898869 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp<sup>3</sup> )-H Bonds*.

Murugesan Kathiravan K   Donabauer Karsten K   König Burkhard B  

Angewandte Chemie (International ed. in English) 20201201 5


The metal-free activation of C(sp<sup>3</sup> )-H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the  ...[more]

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