[reaction: see text]. The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and aryl TBDMS (or TMS) ethers has been shown to be efficiently promoted by proazaphosphatranes such as P(i-BuNCH(2)CH(2))(3)N (3). Excellent yields of diaryl ether products were obtained under unusually mild conditions.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol051108sDOI Listing

Publication Analysis

Top Keywords

nucleophilic aromatic
8
aromatic substitution
8
substitution reaction
8
aryl fluorides
8
fluorides aryl
8
aryl tbdms
8
tbdms tms
8
tms ethers
8
pi-bunch2ch23n efficient
4
efficient promoter
4

Similar Publications

All-carbon quaternary and tertiary stereocenters connected at the C2-position of functionalizable C3-alkylated indole nucleus are commonly occurring frameworks found in many indole alkaloids of medicinal importance. Their direct access is scarcely reported, a long-standing problem, and developing a unique yet simple method can pave the pathway to an entirely different retrosynthetic route for the total synthesis of these alkaloids. Herein, this problem is addressed by developing an unprecedented branch-selective allylation strategy employing a broad range of structurally and electronically different 3-alkenyl-indoles and allylboronic acids.

View Article and Find Full Text PDF

Tetraarylphosphonium Cations with Excellent Alkaline-Resistant Performance for Anion-Exchange Membranes.

ChemSusChem

December 2024

Tokyo Institute of Technology, Department of Chemical Science and Engineering, 4259 G1-9, Nagatsuta, Midori-ku,, 226-8501, Yokohama, JAPAN.

To realize the robust anion exchange membrane (AEM)-based water splitting modules and fuel cells, the design and synthesis of tetraarylphosphonium (TAP) cations are described as a new class of cationic building blocks that exhibit remarkable alkaline stability under harsh conditions. TAP cations with highly sterically demanding aromatic substituents were efficiently synthesized from triarylphosphine derivatives and highly reactive arynes, whose alkaline degradation proved to be suppressed dramatically by the sterically demanding substituents. In the case of bis(2,5-dimethylphenyl)bis(2,4,6-trimethylphenyl)phosphonium, for example, approximately 60% of the cation survived for 27 d under the forced conditions (i.

View Article and Find Full Text PDF

NRPS-like Gene Contributed to the Biosynthesis of Cyclo(Pro-Val) in a Multistress-Tolerant Aromatic Probiotic, GXDK6.

J Agric Food Chem

December 2024

State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, College of Life Science and Technology, Guangxi University, Nanning 530004, China.

Cyclo(Pro-Val) is a diketopiperazine (DKP) found widespread in marine microbes and resulting food products. With new bioactivities of cyclo(Pro-Val) being continually discovered, its potential applications in agriculture and food are becoming more evident, highlighting the need for efficient and practical methods to produce these compounds. However, the biosynthesis mechanisms of cyclo(Pro-Val), particularly in probiotics, remain unclear, and the functional identification of nonribosomal peptide synthases (NRPS) is still limited.

View Article and Find Full Text PDF

Covalent Fragments Acting as Tyrosine Mimics for Mutant p53-Y220C Rescue by Nucleophilic Aromatic Substitution.

ACS Pharmacol Transl Sci

December 2024

Lab for Molecular Design & Pharm. Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls Universität Tübingen, 72076 Tübingen, Germany.

The tumor suppressor p53 is frequently mutated in human cancers. The Y220C mutant is the ninth most common p53 cancer mutant and is classified as a structural mutant, as it leads to strong thermal destabilization and degradation by creating a solvent-accessible hydrophobic cleft. To identify small molecules that thermally stabilize p53, we employed DSF to screen SAr-type electrophiles from our covalent fragment library (CovLib) for binding to different structural (Y220C, R282W) and DNA contact (R273H) mutants of p53.

View Article and Find Full Text PDF

While -phenylenediamine antioxidants (PPDs) pose potential risks to aquatic ecosystems, their environmental persistence and transformation remain ambiguous due to the undefined nature of PPD C-N bond hydrolysis. Here, we investigated the hydrolysis patterns of PPDs by analyzing their hydrolysis half-lives, hydrolysis products around neutral pH (pH 6.0-7.

View Article and Find Full Text PDF

Want 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!