Palladium-CatalyzedC(O)–C Bond Cleavage ofUnstrained Ketones Assisted with Aryl Handles: An Approach to DiarylKetones

C–C bond cleavage reactions have achieved remarkable progress in molecular deconstruction and skeleton editing. In this study, we describe a palladium-catalyzed synthesis of diaryl ketones through a sequence of α-arylation and aerobic oxidative C–C bond cleavage. This transformation features good functional group compatibility, especially for highly reactive groups, including −OH, NH<sub>2</sub>, and −CHO. Furthermore, this approach allows for gram-scale synthesis in a low catalyst loading manner. It also streamlines the synthesis of a variety of drugs or their intermediates. Mechanism studies reveal the essential role of utilizing a bulky ligand and the existence of air as the reaction atmosphere.

Publication Details

Journal
Figshare
Published
2025-03-06
DOI
https://doi.org/10.1021/acs.orglett.5c00455.s001
Primary Topic
Spinal Cord Injury Research
Type
article
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article

Palladium-CatalyzedC(O)–C Bond Cleavage ofUnstrained Ketones Assisted with Aryl Handles: An Approach to DiarylKetones

Figshare
Spinal Cord Injury Research
article

Palladium-CatalyzedC(O)–C Bond Cleavage ofUnstrained Ketones Assisted with Aryl Handles: An Approach to DiarylKetones

article en

Abstract

C–C bond cleavage reactions have achieved remarkable progress in molecular deconstruction and skeleton editing. In this study, we describe a palladium-catalyzed synthesis of diaryl ketones through a sequence of α-arylation and aerobic oxidative C–C bond cleavage. This transformation features good functional group compatibility, especially for highly reactive groups, including −OH, NH<sub>2</sub>, and −CHO. Furthermore, this approach allows for gram-scale synthesis in a low catalyst loading manner. It also streamlines the synthesis of a variety of drugs or their intermediates. Mechanism studies reveal the essential role of utilizing a bulky ligand and the existence of air as the reaction atmosphere.

Figshare
Clean water and sanitation
Openalex Percentile: Top 41%
Spinal Cord Injury Research
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Palladium-CatalyzedC(O)–C Bond Cleavage ofUnstrained Ketones Assisted with Aryl Handles: An Approach to DiarylKetones · Figshare (2025) | TGRS Research Map | TGRS