99758-19-7

Upstream product

• 3857-25-8 2-hydroxymethyl-5-methylfuran 
• 106-96-7 propargyl bromide 

Downstream Products

• 533934-35-9 1,3-dihydro-6-methyl-5-isobenzofuranol 

Relevant academic research and scientific papers

From Furan-Yne Systems to para -Benzoquinone Derivatives: Gold-Catalyzed Cyclization and Oxidation, and Further Reduction by Sodium Dithionate

A series of furan-yne systems were transformed into the corresponding para -benzoquinone derivatives by gold(ΙΙΙ) catalyst. The two-step procedure consisted of a phenol synthesis and subsequent oxidation with iodobenzene diacetate. The reactions can be carried out in a one-pot procedure with the same precatalyst. The para -benzoquinone could simply be converted into the corresponding hydroquinones by reduction with sodium dithionate. This protocol features high efficiency, mild conditions, and wide substrate scopes.

Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones

The reactivity of "furan-ynes"in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinone and a furan enone, has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, thus affording functionalized dihydropyridinones and pyranones.

A New Approach for the Synthesis of Highly Substituted Aromatic Rings: The Alkyne-Mediated Approach

Pentasubstituted aromatic rings serve as templates for drug design and can be conveniently prepared by the thermolysis of suitably substituted alkynes under microwave conditions. Rings in the microwave! Pentasubstituted aromatic rings serve as templates for drug design and can be conveniently prepared by the thermolysis of suitably substituted alkynes under microwave conditions.

New and easily accessible nitrogen acyclic gold(I) carbenes: Structure and application in the gold-catalyzed phenol synthesis as well as the hydration of alkynes

A series of gold(I) isonitrile complexes were prepared and converted to the corresponding diaminocarbene gold(I) complexes by reactions with primary and symmetrical secondary amines. Twelve crystal structure analyses of the gold(I) complexes could be obtained, in addition NMR studies allowed an analysis of the different diastereomers present in solution. In the gold-catalyzed phenol synthesis these complexes were very successful as pre-catalysts, reaching an unprecedented 3050 turnovers with a problematic substrate. Good conversions in the hydration of phenylacetylene could also be achieved.

Gold catalysis: Dihydroisobenzofurans and isochromanes by the intramolecular furan/alkyne reaction

A series of furyl alcohols and homofuryl alcohols was synthesized by reduction of furfurals or reaction of furyllithium compounds with epoxides and subsequent propargylation. The gold-catalyzed cycloisomerization of these products furnished dihydroisobenzofurans and isochromanes. Crystal structure analyses proved the sequence of the substituents for both classes of products. Unsaturated dicarbonyl compounds as side-products show the mechanistic relationship to the analogous platinum-catalyzed reactions. Neither ester groups, even on the 4-position of the furan ring, nor aryl bromides hinder the catalysis by gold. In the case of a substrate with an allyl ether in the side chain, a side-product, which provides evidence for a reaction of the alkyne with an inverse regioselectivity, was observed.

Intramolecular reactions of alkynes with furans and electron rich arenes catalyzed by PtCl2: The role of platinum carbenes as intermediates

5-(2-Furyl)-1-alkynes react, with PtCl2 as catalyst, to give phenols. On the basis of DFT calculations, a cyclopropyl platinacarbene complex was found as the key intermediate in the process. The cyclopropane and dihydrofuran rings of this intermediate open to form a carbonyl compound, which reacts with the platinum carbene to form an oxepin, which is in equilibrium with an arene oxide. When the reaction is carried out in the presence of water, dicarbonyl compounds are obtained, which support the proposed mechanism. Other cyclizations of alkynes with furans or electron-rich arenes give products of apparent Friedel-Crafts-type reactions, although these processes could also proceed by pathways involving the formation of cyclopropyl platinum carbenes.