Herein, a new strategy for the direct synthesis of functionalized pyrroles from β-amino alcohols and ynones ruthenium-catalyzed acceptorless dehydrogenative coupling has been demonstrated. This developed methodology proceeds in an atom- and step-economic fashion together with the merits of broad substrate scope, operational simplicity, and water and hydrogen gas as the sole by-products, which provides an alternative and sustainable way to access functionalized pyrroles. Further, this method was applied to the rapid synthesis of the COX-1/COX-2 inhibitor and boron dipyrromethene derivative successfully.
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http://dx.doi.org/10.1039/d1cc07018e | DOI Listing |
Dalton Trans
January 2025
Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, c/Maria Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain.
The oxalamide skeleton is a common structural motif in many biologically active molecules. These scaffolds can be synthesized ruthenium pincer complex-catalyzed acceptorless dehydrogenative coupling of ethylene glycol and amines. In this study, we elucidate the mechanism of this oxalamide synthesis using density functional theory calculations.
View Article and Find Full Text PDFOrg Lett
November 2024
Key Laboratory of Green Chemistry & Technology, Ministry of Education College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Described herein is the synthesis of 2-pyrazolines via acceptorless dehydrogenative coupling of allylic alcohols with hydrazines based on a Ru(CO)/NHC-phosphine-phosphine ligand catalytic system. The reaction not only exhibits low catalyst loading (only 0.3 mol %), wide substrate scope, good to excellent yields, and high selectivity but also omits the use of sacrificial hydrogen acceptor with only H and HO as byproducts, making the reaction green and atom-economical.
View Article and Find Full Text PDFChem Asian J
October 2023
School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, 752050, India.
A catalytic method for the direct synthesis of oximes from alcohols and hydroxyl amine hydrochloride salt is reported. The reaction is catalyzed by a ruthenium pincer catalyst, which oxidizes alcohols involving amine-amide metal-ligand cooperation, and the in situ formed aldehydes condense with hydroxyl amine to deliver the oximes. Notably, the reaction requires only a catalyst and base; water and liberated hydrogen are the only byproducts, making this protocol attractive and environmentally benign.
View Article and Find Full Text PDFOrg Lett
June 2022
Key Laboratory of Green Chemistry & Technology, Ministry of Education College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People's Republic of China.
Herein, the divergent transformations of 1,3-diols with arylhydrazines via acceptorless dehydrogenative coupling reactions to selectively synthesize pyrazoles and 2-pyrazolines were reported, which were based on Ru(CO)/NHC-phosphine-phosphine catalytic systems. The reactions featured low catalyst loading, high selectivity, wide substrate scope, and good yields, with only water and hydrogen gas (H) as the byproducts.
View Article and Find Full Text PDFChem Sci
March 2022
Department of Molecular Chemistry and Materials Science, Weizmann Institute of Science Rehovot 76100 Israel
The highly desirable synthesis of the widely-used primary amides directly from alcohols and ammonia acceptorless dehydrogenative coupling represents a clean, atom-economical, sustainable process. Nevertheless, such a reaction has not been previously reported, and the existing catalytic systems instead generate other N-containing products, , amines, imines and nitriles. Herein, we demonstrate an efficient and selective ruthenium-catalyzed synthesis of primary amides from alcohols and ammonia gas, accompanied by H liberation.
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