2,5-Disubstituted furans from 1,4-alkynediols

Pridmore, Simon J.; Slatford, Paul A.; Williams, Jonathan M. J.

doi:10.1016/j.tetlet.2007.05.069

Cited by 44 publications

(14 citation statements)

References 18 publications

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“…Methyl 4-(5-methylfuran-2-yl)benzoate (25): [50] Compound 25 was prepared from methyl 4-aminobenzoate and 24 according to the modified procedure described for the preparation of 23. To increase the solubility of 24 in the aqueous phase, CH 3 CN (18 mL) was added.…”

Section: General Procedures For the Radical Arylationmentioning

confidence: 99%

Radical Arylation of Phenols, Phenyl Ethers, and Furans

Wetzel

Pratsch

Kolb

et al. 2010

Chemistry A European J

108

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Radical arylations of para-substituted phenols and phenyl ethers proceeded with good regioselectivity at the ortho position with respect to the hydroxy or alkoxy group. The reactions were conducted with arenediazonium salts as the aryl radical source, titanium(III) chloride as the reductant, and diluted hydrochloric acid as the solvent. Substituted biaryls were obtained from hydroxy- and alkoxy-substituted benzylamines, phenethylamines, and aromatic amino acids. The methodology described offers a fast, efficient, and cost-effective new access to diversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxy groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a beta-secretase inhibitor and the synthesis of a calcium-channel modulator.

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Section: General Procedures For the Radical Arylationmentioning

confidence: 99%

Radical Arylation of Phenols, Phenyl Ethers, and Furans

Wetzel

Pratsch

Kolb

et al. 2010

Chemistry A European J

108

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“…Preliminary results indicated that Ru(PPh 3 ) 3 (CO)H 2 / xantphos was a more effective catalyst than other Ru and Ir complexes that we had screened. 27 2. Results and discussion 2.1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation

et al. 2009

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“…[Ru(PPh 3 ) 3 (CO)H 2 ]inassociation with Xantphos was utilized for isomerization of 1,4-alkynediols into 1,4-diketones (87) which then undergo acid-catalyzed dehydration, thus providing ar ange of 2,5-disubstituted furans (88;S cheme 12). [41] Krische et al reported the enantioselective synthesis of a-exo-methylene g-butyrolactones (90)through aC À Cbondforming reaction of acrylic esters and alcohols by using ac yclometallated chiral iridium complex (89)u nder mild reaction conditions for ac arbonyl 2-(alkoxycarbonyl)allylation [Eq. (26)].…”

Section: Annulation Of Alcohols With Unsaturated Systemsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Hydrogen‐Transfer Annulations: Access to Heterocyclic Scaffolds

et al. 2015

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The ability of hydrogen-transfer transition-metal catalysts, which enable increasingly rapid access to important structural scaffolds from simple starting materials, has led to a plethora of research efforts on the construction of heterocyclic scaffolds. Transition-metal-catalyzed hydrogen-transfer annulations are environmentally benign and highly atom-economical as they release of water and hydrogen as by-product and utilize renewable feedstock alcohols as starting materials. Recent advances in this field with respect to the annulations of alcohols with various nucleophilic partners, thus leading to the formation of heterocyclic scaffolds, are highlighted herein.

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2,5-Disubstituted furans from 1,4-alkynediols

Cited by 44 publications

References 18 publications

Radical Arylation of Phenols, Phenyl Ethers, and Furans

Radical Arylation of Phenols, Phenyl Ethers, and Furans

Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation

Transition‐Metal‐Catalyzed Hydrogen‐Transfer Annulations: Access to Heterocyclic Scaffolds

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