The key carbenoid intermediate of transition-metal-catalyzed furan-yne cyclization in Hashmi phenol synthesis could be efficiently intercepted with water under the developed reaction conditions in order to provide access to functionalized unsaturated dicarbonyl compounds that might serve as convenient precursors for the straightforward synthesis of annulated pyridazines.
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Interrupted Furan-Yne Cyclization: Access to Unsaturated Dicarbonyl Compounds and Their Subsequent Transformation into Functionalized Pyridazines.
Org Lett
November 2023
Department of Chemistry, Perm State University, Bukireva 15, 614990 Perm, Russia.
The key carbenoid intermediate of transition-metal-catalyzed furan-yne cyclization in Hashmi phenol synthesis could be efficiently intercepted with water under the developed reaction conditions in order to provide access to functionalized unsaturated dicarbonyl compounds that might serve as convenient precursors for the straightforward synthesis of annulated pyridazines.
View Article and Find Full Text PDFAccess to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N-(2-Furanylmethyl) Alkynamides under Air.
Org Lett
April 2018
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology, Guangzhou 510640 , P. R. China.
A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan-yne cyclization at room temperature in air and may proceed via nucleopalladation of the alkyne to form a vinylpalladium intermediate, with a furan ring acting as the nucleophile.
View Article and Find Full Text PDFGold-Catalyzed Cyclization of Furan-Ynes bearing a Propargyl Carbonate Group: Intramolecular Diels-Alder Reaction with In Situ Generated Allenes.
Chemistry
September 2016
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, People's Republic of China), Fax: (+86) 021-64166128.
Gold-catalyzed cyclization of various furan-ynes with a propargyl carbonate or ester moiety results in the formation of a series of polycyclic aromatic ring systems. The reactions can be rationalized through a tandem gold-catalyzed 3,3-rearrangement of the propargyl carboxylate moiety in furan-yne substrates to form an allenic intermediate, which is followed by an intramolecular Diels-Alder reaction of furan and subsequent ring-opening of the oxa-bridged cycloadduct. It was found that the steric and electronic properties of phosphine ligands on the gold catalyst had a significant impact on the reaction outcome.
View Article and Find Full Text PDFGold(I)-catalyzed furan-yne cyclizations involving 1,2-rearrangement: efficient synthesis of functionalized 1-naphthols and its application to the synthesis of wailupemycin G.
Chemistry
September 2014
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China), Fax: (+86) 021-64166128.
Gold-catalyzed cascade cyclization/1,2-rearrangement of 1-(2-furanyl)phenyl propargyl alcohols has been developed, which provides a rapid and efficient access to multisubstituted 1-naphthols bearing an enal or enone moiety with high stereoselectivity. The (Z)- or (E)-stereochemistry can be easily controlled by choosing protected- or non-protected substrates. The utility of the methodology has been illustrated in the first total synthesis of wailupemycin G.
View Article and Find Full Text PDFHighly active phosphite gold(I) catalysts for intramolecular hydroalkoxylation, enyne cyclization and furanyne cyclization.
Chem Commun (Camb)
May 2014
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
New and highly active mononuclear phosphite gold(I) catalysts are described. Turn-over numbers up to 37,000 for the furan-yne reaction and up to 28,000,000 for the two-fold hydroalkoxylation of alkynes are reported.
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