Preparation of α-Acyloxy Ketones via Visible-Light-Driven Aerobic Oxo-Acyloxylation of Olefins with Carboxylic Acids.

Org Lett

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, P. R. China.

Published: October 2016

We developed a visible-light driven oxo-acyloxylation of aryl alkenes with carboxylic acids and molecular oxygen. A metal-free photoredox system, consisting of an acridinium photocatalyst, an organic base, and molecular sieve (MS) 4 Å, promotes chemoselective aerobic photooxidation of aryl alkenes. This approach may provide a green, practical, and metal-free protocol for a wide range of α-acyloxy ketones.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.6b02560DOI Listing

Publication Analysis

Top Keywords

α-acyloxy ketones
8
carboxylic acids
8
aryl alkenes
8
preparation α-acyloxy
4
ketones visible-light-driven
4
visible-light-driven aerobic
4
aerobic oxo-acyloxylation
4
oxo-acyloxylation olefins
4
olefins carboxylic
4
acids developed
4

Similar Publications

Regioselective 1,4-Addition of P(O)-H Species to In SituFormed 1-Benzopyrylium Ion from C3-Substituted 2-Chromene Hemiketals to Construct C3-Functionalized C4-Phosphorylated 4-Chromenes.

J Org Chem

January 2025

Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, 2025 Chengluo Avenue, Chengdu 610016, P.R. China.

Herein, we report the first example that P(O)-H species including -phosphonates and -phosphine oxides could participate in a highly regioselective 1,4-addition to in situ generated 1-benzopyrylium ion from C3-substituted 2-chromene hemiketals, which provides a brand-new and effective approach for the synthesis of C4-phosphorylated 4-chromenes with diverse C3-functionality (ketone, ester, sulfonyl, aryl, and alkyl groups). In total, the reaction features the use of inexpensive Zn(ClO)·6HO as a catalyst, low catalyst loading (only 5 mol %), mild reaction conditions (60 °C, 10 min to 24 h), and broad substrate scope (46 examples) as well as good to high yields (>90% yield on average). More importantly, mechanistic experiments demonstrated the essential role of the C3-substituent on 2-chromene hemiketals in stabilizing the in situ generated 1-benzopyrylium ion and the regioselective 1,4-addition control.

View Article and Find Full Text PDF

While polyetherketoneketone is a high-performance thermoplastic polymer, its hydrophobicity and inertness limit bone adhesion. This study aimed to evaluate a novel PEKK/CaSiO/TeO nanocomposite, comparing it to PEKK/15 wt.% CaSiO and PEKK groups.

View Article and Find Full Text PDF

Analyzing the effect of different storage times and different processes on the volatile components in Shenling Baizhu powder by HS-GC-IMS combined with multivariate statistics.

Anal Methods

January 2025

Shaanxi Province Key Laboratory of New Drugs and Chinese Medicine Foundation Research, Pharmacy College, Shaanxi University of Chinese Medicine, No. 1, Shiji Avenue, Xi Xian New District, Xi'an City, 712046 Xianyang, Shaanxi Province, China.

Aim: this study aimed to examine the effect of different storage times (0, 7, 24, 57, and 119 days) on the volatile components of Shenling Baizhu powder across different preparation processes (Pharmacopoeia, ultra-micro pulverization-pulverization, and microparticle design methods). The findings offer insights to guide quality control measures for Shenling Baizhu powder.

Methods: gas chromatography-ion mobility spectrometry (GC-IMS) was employed to ascertain the volatile components in Shenling Baizhu powder at various storage times across different preparation processes.

View Article and Find Full Text PDF

Hereditary tyrosinemia type 1 (HT-1) is an inborn error of metabolism caused by a defect in tyrosine (tyr) degradation. This defect results in the accumulation of succinylacetone (SA), causing liver failure with a high risk of hepatocarcinoma and kidney injury, leading in turn to Fanconi syndrome with urine loss of phosphate and secondary hypophosphatemic rickets (HR). HT-1 diagnosis is usually made in infants with acute or chronic liver failure or by neonatal screening programs.

View Article and Find Full Text PDF

In this study, we present a novel approach using amperometric microsensors to detect quercetin in cosmetic formulations and track its metabolic behavior after topical application. This method offers a sensitive, real-time alternative to conventional techniques, enabling the detection of quercetin's bioavailability, its transformation into active metabolites, and its potential therapeutic effects when applied to the skin. Quercetin (Q) is a bioactive flavonoid known for its potent antioxidant properties, naturally present in numerous plants, particularly those with applications in cosmetic formulations.

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!