A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity.
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http://dx.doi.org/10.1021/ol302586m | DOI Listing |
Chem Commun (Camb)
December 2024
School of Chemistry, University College Dublin, Science Centre South, Dublin 4, Ireland.
We report a continuous flow approach generating bicyclic cyclobutanes from unactivated alkenes in a metal-free manner that is inspired by the Kochi-Salomon reaction. A filtered Hg-lamp in combination with a simple flow set-up and acetone as UV light-absorbing co-solvent are crucial for this method thus showcasing attractive features for further exploitations.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Czech Academy of Sciences: Akademie ved Ceske republiky, Organic Chemistry and Biochemistry, 16000, CZECHIA.
J Org Chem
December 2024
Department of Discovery Analytical Research, Merck & Co., Inc., South San Francisco, California 94080, United States.
A method to access highly substituted dihydrothiophenes and the corresponding thiophenes is reported. This strategy complements traditional stepwise synthesis by coupling readily accessible bicyclic 1,2,3 thiadiazoles with alkenes in a modular, Rh-catalyzed formal (3 + 2) cycloaddition. Application of this method to an array of novel thiadiazoles generates densely functionalized dihydrothiophenes that can be subsequently oxidized to the corresponding thiophene products.
View Article and Find Full Text PDFEnzyme Microb Technol
February 2025
Laboratory of Biocatalysis and Synthetic Biotechnology, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China.
Lipase can mediate the chemo-enzymatic epoxidation of alkenes with the presence of free carboxylic acid and hydrogen peroxide. Four novel lipases with the abilities of chemo-enzymatic epoxidation were mined from the gene database. Lipase TiL originated from Tilletia indica was identified with significant activity on formation of methyl epoxystearate from methyl oleate.
View Article and Find Full Text PDFChem Sci
November 2024
School of Chemistry and Molecular Biosciences, University of Queensland Brisbane 4072 Queensland Australia
In 1981, Maier and Schleyer first identified a select number of cage bicyclic olefins (alkenes) as "hyperstable", and predicted them to be "remarkably unreactive", based solely on theoretical methods. Since that time only three systems meeting the criteria of a hyperstable alkene have been reported in the literature. A one-pot, telescoped synthesis, of four hyperstable alkenes is reported herein, which has uncovered unexpected reactivity towards oxidation.
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