[reaction: see text] The coupling of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles, either catalyzed by AuCl3 or induced by an electrophile, provides highly substituted furans in good to excellent yields under very mild reaction conditions Various nucleophiles, including functionally substituted alcohols, H2O, carboxylic acids, 1,3-diketones, and electron-rich arenes, and a range of cyclic and acyclic 2-(1-alkynyl)-2-alken-1-ones readily participate in these cyclizations Iodine, NIS, and PhSeCl have proven successful as electrophiles in this process The resulting iodine-containing furans can be readily elaborated to more complex products using known organopalladium chemistry

Synthesis of Highly Substituted Furans by the Electrophile-Induced Coupling of 2-(1-Alkynyl)-2-alken-1-ones and Nucleophiles

Described herein is the Pd0-catalyzed coupling cyclization reaction of 1,2-allenyl ketones with organic halides leading efficiently and conveniently to not only 2,3,4- and 2,3,5-trisubstituted furans but also 2,3,4,5-tetrasubstituted furans Furthermore, this method showed high substituent-loading capability and tolerance of various substituents The reactions of 1,2-allenyl ketones 1 e, 1 p, 1 q, and deuterated [D]1 c were performed for a mechanistic study, which demonstrated that instead of an enolization pathway, the reaction may proceed via the intermediacy of dienolate palladium and intramolecular nucleophilic attack on the π-allyl palladium intermediate by the carbonyl oxygen

Pd0‐Catalyzed Coupling Cyclization Reaction of Aryl or 1Alkenyl Halides with 1,2‐Allenyl Ketones: Scope and Mechanism. An Efficient Assembly of 2,3,4‐, 2,3,5‐Tri‐ and 2,3,4,5‐Tetrasubstituted Furans

Electrophilic cyclization of 2-(1-alkynyl)-2-alken-1-ones using the I2/K3PO4 system: an efficient synthesis of highly substituted iodofurans.

This chapter discusses the various methods for the preparation of oxabicyclic compounds, with an emphasis on the stereo- and enantioselective synthesis of these substances. Methods to desymmetrize meso oxabicyclic compounds are also presented. The utility of these substrates for organic synthesis is demonstrated by the many strategies available for ring-opening the bicyclic compounds to yield cyclic and acyclic structures. Examples demonstrating how this strategy has been incorporated into the efficient syntheses of many natural products are presented.

Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis

A new three-component cyclization-coupling reaction catalyzed by palladium was developed, producing polysubstituted furans in good yields from readily available substrates. The reaction conditions and the scope of the process were examined, and a possible mechanism is proposed.

Palladium-catalyzed one-pot synthesis of highly substituted furans by a three-component annulation reaction.

3.11 – Furans and their Benzo Derivatives: (ii) Reactivity

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3.11 – Furans and their Benzo Derivatives: (ii) Reactivity