Light-driven transition-metal-free direct decarbonylation of unstrained diaryl ketones via a dual C–C bond cleavage

Dawei Cao, Mohamad Ataya, Zhangpei Chen, Huiying Zeng, Yong Peng, Rustam Z. Khaliullin () and Chao-Jun Li ()
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Dawei Cao: McGill University
Mohamad Ataya: McGill University
Zhangpei Chen: McGill University
Huiying Zeng: Lanzhou University
Yong Peng: Lanzhou University
Rustam Z. Khaliullin: McGill University
Chao-Jun Li: McGill University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract The cleavage and formation of carbon−carbon bonds have emerged as powerful tools for structural modifications in organic synthesis. Although transition−metal−catalyzed decarbonylation of unstrained diaryl ketones provides a viable protocol to construct biaryl structures, the use of expensive catalyst and high temperature (>140 oC) have greatly limited their universal applicability. Moreover, the direct activation of two inert C − C bonds in diaryl ketones without the assistance of metal catalyst has been a great challenge due to the inherent stability of C − C bonds (nonpolar, thermo-dynamically stable, and kinetically inert). Here we report an efficient light-driven transition-metal-free strategy for decarbonylation of unstrained diaryl ketones to construct biaryl compounds through dual inert C − C bonds cleavage. This reaction featured mild reaction conditions, easy-to-handle reactants and reagents, and excellent functional groups tolerance. The mechanistic investigation and DFT calculation suggest that this strategy proceeds through the formation of dioxy radical intermediate via a single-electron-transfer (SET) process between photo-excited diaryl ketone and DBU mediated by DMSO, followed by removal of CO2 to construct biaryl compounds.

Date: 2022
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DOI: 10.1038/s41467-022-29327-z

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