Palladium-Catalyzed Synthesis of Linked Bis-HeterocyclesSynthesis and Investigation of Photophysical Properties

A palladium-catalyzed domino C–N coupling/Cacchi reaction is reported. Design of photoluminescent bis-heterocycles, aided by density functional theory calculations, was performed with synthetic yields up to 98%. The photophysical properties of the products accessed via this strategy were part of a c...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2023-12, Vol.145 (49), p.26623-26631
Main Authors: Arora, Ramon, Mirabi, Bijan, Durant, Andrew G., Bozal-Ginesta, Carlota, Marchese, Austin D., Aspuru-Guzik, Alán, Lautens, Mark
Format: Article
Language:English
Subjects:
density functional theory
photoluminescence
society
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Summary:A palladium-catalyzed domino C–N coupling/Cacchi reaction is reported. Design of photoluminescent bis-heterocycles, aided by density functional theory calculations, was performed with synthetic yields up to 98%. The photophysical properties of the products accessed via this strategy were part of a comprehensive study that led to broad emission spectra and quantum yields of up to 0.59. Mechanistic experiments confirmed bromoalkynes as competent intermediates, and a density functional theory investigation suggests a pathway involving initial oxidative addition into the cis C–Br bond of the gem-dihaloolefin.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c07234