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. 2024 May 14;15(24):9155-9163.
doi: 10.1039/d4sc00904e. eCollection 2024 Jun 19.

Mechanochemical synthesis of aromatic ketones: pyrylium tetrafluoroborate mediated deaminative arylation of amides

Satenik Mkrtchyan  1 , Oleksandr Shalimov  2 , Michael G Garcia  3 , Jiří Zapletal  1 , Viktor O Iaroshenko  1   4   5   6
Affiliations

Mechanochemical synthesis of aromatic ketones: pyrylium tetrafluoroborate mediated deaminative arylation of amides

Satenik Mkrtchyan et al. Chem Sci. .

Abstract

A new method has been introduced that is able to tackle the complexities of N-C(O) activation in amide moieties through utilization of pyrylium tetrafluoroborate in a mechanochemical setting, where amide bonds undergo activation and subsequent conversion to biaryl ketones. Due to the employment of a mechanochemical setting, the reaction conforms to green chemistry principles, offering an environmentally friendly approach to traditional amide derivatization techniques that rely on transition metals to achieve further functionalization.

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Conflict of interest statement

The authors declare no competing financial interests.

Figures

Scheme 1
Scheme 1. Sample reported strategies for amide bond functionalization and our concept.
Scheme 2
Scheme 2. Scope of aromatic ketones.
Scheme 3
Scheme 3. Scope of aromatic amides.
Scheme 4
Scheme 4. Mechanism of deaminative arylation of aryl amides.
See this image and copyright information in PMC

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