Mercury(II) trifluoroacetate-mediated cyclisation of aryl allenic ethers
TL;DR: Mercury(II) trifluoroacetate brings about a facile cyclisation of aryl allenic(aryl 2,3-butadien-1yl) ethers to 4-methyl-2H-1-benzopyrans.
About: This article is published in Tetrahedron Letters.The article was published on 1991-11-04. It has received 17 citations till now. The article focuses on the topics: Aryl & Mercury (element).
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TL;DR: The electrophilic cyclization of substituted propargylic aryl ethers by I2, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields.
Abstract: The electrophilic cyclization of substituted propargylic aryl ethers by I2, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields. This methodology results in vinylic halides or selenides under mild reaction conditions and tolerates a variety of functional groups, including methoxy, alcohol, aldehyde, and nitro groups.
140 citations
TL;DR: Gold-catalyzed intramolecular hydroarylation of allenic anilines and phenols offers an efficient route to dihydroquinoline and chromene derivatives under mild reaction conditions, leading to a highly selective formation of six-membered rings.
110 citations
TL;DR: In this paper, a variety of mono-and disubstituted phenols are alkylated with propargyl bromide to give phenyl 2-propynyl ethers, which were further coupled with aryl iodides under Sonogashira reaction conditions to give 3-phenoxy-1-aryl-1propyne derivatives.
37 citations
TL;DR: In this article, N-alkyl-N-allenylmethylanilines with magnesium monoperoxyphthalate in methanol-water underwent tandem transformations to furnish Nalkyl 2-ethenylindoles in good yield.
Abstract: Treatment of N-alkyl-N-allenylmethylanilines with magnesium monoperoxyphthalate in methanol–water underwent tandem transformations to furnish N-alkyl-2-ethenylindoles in good yield.
16 citations
TL;DR: In this paper, a stereocontrolled synthetic approach to E and Z -substituted methylene-3,4-dihydro-2 H -1-benzopyrans is described from acyclic derivatives using as a key step the palladium-catalyzed intramolecular cyclic carbopalladation of iodoalkynes.
12 citations
References
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TL;DR: Le (bis-[(bromo-4 di-t-butyl-2,6)phenoxy methyl) aluminium peut etre utilise pour obtenir l'isomere (Z) alors que l'sisomeres (E) est produit avec le (bis-(diphenyl 2,6 phenoxy] methyl) aluminum as discussed by the authors.
Abstract: Le (bis-[(bromo-4 di-t-butyl-2,6)phenoxy methyl) aluminium peut etre utilise pour obtenir l'isomere (Z) alors que l'isomere (E) est produit avec le (bis-[diphenyl-2,6 phenoxy] methyl) aluminium
113 citations
110 citations
TL;DR: This is the first to show that meta-Claisen rearrangement occurs preferentially even when a free para position is available, and can be interpreted in terms of the small bond energy of the breaking apical carbon-iodine (III) bond.
Abstract: Reported for the first time are the generation of allenyliodinanes and their reductive iodonio-Claisen rearrangement Reaction of propargylsilanes, germanes, and stannanes with aryliodinanes in the presence of BF 3 -Et 2 O undergoes a reductive iodonio-Claisen rearrangement under mild conditions, yielding o-propargyliodoarenes in good yields The reductive ortho propargylation probably involves the intermediate formation of allenyl(aryl) iodinanes, which undergo [3,3]-sigmatropic rearrangement The lack of crossover products argues for the intramolecularity of the rearrangement When both ortho positions of aryliodinanes are occupied with alkyl substituents, the reductive iodonio-Claisen rearrangement affords meta substitution products This is the first to show that meta-Claisen rearrangement occurs preferentially even when a free para position is available The reductive ortho propargylation of iodinanes takes place under much milder conditions than the Claisen rearrangement The lower activation energy associated with the iodonio-Claisen rearrangement of allenyl(aryl) iodinanes can be interpreted in terms of the small bond energy of the breaking apical carbon-iodine (III) bond
65 citations
TL;DR: Les cyclisations sont obtenues par reaction avec la piperidine ou la triethylamine in presence of a catalyseur au palladium as discussed by the authors.
Abstract: Les cyclisations sont obtenues par reaction avec la piperidine ou la triethylamine en presence d'un catalyseur au palladium: obtention d'heterocycles azotes ou oxygenes a 5, 6 ou 7 chainons
64 citations
39 citations