Direct transformations of diarylketones to hetero- and carbofunctionalized diarylmethanes have been developed. The reactions involve a phospha-Brook rearrangement of diphenylphosphine oxide with diarylketones, followed by substitutions with various nucleophiles such as amides, amines, phenols, thiols, and diborylmethane under palladium catalysis to afford the corresponding functionalized diarylmethanes in a reductive manner.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.4c00831 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electroreductive alkylations of (hetero)arenes with carboxylic acids.
Nat Commun
June 2024
College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, 410082, Changsha, China.
Carboxylic acids are widely available and generally inexpensive from abundant biomass feedstocks, and they are suitable and generic coupling partners in synthetic chemistry. Reported herein is an electroreductive coupling of stable and versatile carboxylic acids with (hetero)arenes using protons as the hydrogen source. The application of an earth-abundant titanium catalyst has significantly improved the deoxygenative reduction process.
View Article and Find Full Text PDFDeoxygenative Hetero- and Carbofunctionalizations of Diarylketones.
J Org Chem
June 2024
Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.
Direct transformations of diarylketones to hetero- and carbofunctionalized diarylmethanes have been developed. The reactions involve a phospha-Brook rearrangement of diphenylphosphine oxide with diarylketones, followed by substitutions with various nucleophiles such as amides, amines, phenols, thiols, and diborylmethane under palladium catalysis to afford the corresponding functionalized diarylmethanes in a reductive manner.
View Article and Find Full Text PDFSynthesis of γ-Oxo-α-amino Acids via Radical Acylation with Carboxylic Acids.
J Org Chem
June 2021
Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany.
Herein we present a highly efficient, light-mediated, deoxygenative protocol to access γ-oxo-α-amino acid derivatives. This radical methodology employs photoredox catalysis, in combination with triphenylphosphine, to generate acyl radicals from readily available (hetero)aromatic and vinylic carboxylic acids. This approach allows for the straightforward synthesis of γ-oxo-α-amino acids bearing a wide range of functional groups (e.
View Article and Find Full Text PDFPEt-Mediated Deoxygenative C-N Coupling of Nitroarenes and Boronic Acids.
Tetrahedron
June 2019
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
A method for the preparation of aryl- and heteroarylamine products by triethylphosphine-mediated deoxygenative coupling of nitroarenes and boronic acids is reported. This method provides access to an array of functionalized (hetero)arylamine products from readily available starting materials under the action of an inexpensive commercial reagent. The developed triethylphosphine-mediated transformation highlights the capability of organophosphorus compounds to carry out this useful deoxygenative transformation without the necessity of any transition metal additives.
View Article and Find Full Text PDFDegradation of Diphenyl Ether in Sphingobium phenoxybenzoativorans SC_3 Is Initiated by a Novel Ring Cleavage Dioxygenase.
Appl Environ Microbiol
May 2017
The College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, Jiangsu, China
SC_3 degrades and utilizes diphenyl ether (DE) or 2-carboxy-DE as its sole carbon and energy source. In this study, we report the degradation of DE and 2-carboxy-DE initiated by a novel ring cleavage angular dioxygenase (diphenyl ether dioxygenase [Dpe]) in the strain. Dpe functions at the angular carbon and its adjacent carbon (C-1a, C-2) of a benzene ring in DE (or the 2-carboxybenzene ring in 2-carboxy-DE) and cleaves the C-1a-C-2 bond (decarboxylation occurs simultaneously for 2-carboxy-DE), yielding 2,4-hexadienal phenyl ester, which is subsequently hydrolyzed to muconic acid semialdehyde and phenol.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!