Synthesis of -acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts.

Beilstein J Org Chem

Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany.

Published: January 2024

-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in -xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other -heterocycles, such as acridines, phenoxazines, or phenazines, showcasing the robustness of our technique. In a broader sense, this new method creates two C-N bonds simultaneously based on a mono-halogenated starting material, thus allowing heterocycle formation with diminished halogen waste

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10777325PMC
http://dx.doi.org/10.3762/bjoc.20.2DOI Listing

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Synthesis of -acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts.

Beilstein J Org Chem

January 2024

Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany.

-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in -xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates.

View Article and Find Full Text PDF

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