A silver-based catalyst system has been discovered that effectively promotes the protodecarboxylation of various carboxylic acids at temperatures of 80-120 degrees C--more than 50 degrees C below those of the best known copper catalysts.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/b912509d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
ORGANOMETALLIC GAS-PHASE ION CHEMISTRY AND CATALYSIS: INSIGHTS INTO THE USE OF METAL CATALYSTS TO PROMOTE SELECTIVITY IN THE REACTIONS OF CARBOXYLIC ACIDS AND THEIR DERIVATIVES.
Mass Spectrom Rev
November 2021
School of Chemistry, University of Melbourne, Victoria, 3010, Australia.
Carboxylic acids are valuable organic substrates as they are widely available, easy to handle, and exhibit structural and functional variety. While they are used in many standard synthetic protocols, over the past two decades numerous studies have explored new modes of metal-mediated reactivity of carboxylic acids and their derivatives. Mass spectrometry-based studies can provide fundamental mechanistic insights into these new modes of reactivity.
View Article and Find Full Text PDFDirect reversible decarboxylation from stable organic acids in dimethylformamide solution.
Science
July 2020
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Many classical and emerging methodologies in organic chemistry rely on carbon dioxide (CO) extrusion to generate reactive intermediates for bond-forming events. Synthetic reactions that involve the microscopic reverse-the carboxylation of reactive intermediates-have conventionally been undertaken using very different conditions. We report that chemically stable C(sp) carboxylates, such as arylacetic acids and malonate half-esters, undergo uncatalyzed reversible decarboxylation in dimethylformamide solution.
View Article and Find Full Text PDFOn/Off O Switchable Photocatalytic Oxidative and Protodecarboxylation of Carboxylic Acids.
J Org Chem
November 2019
Department of Chemistry , Shiraz University, Shiraz 7194684795 , I. R. Iran.
Photoredox catalysis in recent years has manifested a powerful branch of science in organic synthesis. Although merging photoredox and metal catalysts has been a widely used method, switchable heterogeneous photoredox catalysis has rarely been considered. Herein, we open a new window to use a switchable heterogeneous photoredox catalyst which could be turned on/off by changing a simple stimulus (O) for two opponent reactions, namely, oxidative and protodecarboxylation.
View Article and Find Full Text PDFHighly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons palladium catalysis.
Chem Sci
June 2019
College of Chemistry and Chemical Engineering and Key Laboratory of Auxiliary Chemistry and Technology for Chemical Industry , Ministry of Education , Shaanxi University of Science and Technology, Xi'an 710021 , China.
Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism.
View Article and Find Full Text PDFPd-Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid.
Chemistry
July 2019
Fakultät Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstr. 150, 44801, Bochum, Germany.
Acrylic acid is presented as an inexpensive, non-volatile vinylating agent in a palladium-catalyzed decarboxylative vinylation of aryl halides. The reaction proceeds through a Heck reaction of acrylic acid, immediately followed by protodecarboxylation of the cinnamic acid intermediate. The use of the carboxylate group as a deciduous directing group ensures high selectivity for monoarylated products.
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!