Stereomutation in the Seyferth reaction

Lambert, Joseph B.; Larson, Eric G.; Bosch, Richard J.; TeVrucht, Mollie L. E.

doi:10.1021/ja00305a019

Cited by 13 publications

(4 citation statements)

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“…Commercially available alkynes (Aldrich, ACROS, Lancaster) were dried (CaH 2 or molecular sieves) and distilled. p ‐Chlorophenylacetylene23 and p ‐methoxyphenylacetylene24 were prepared according to literature procedures. All phosphorus ligands are commercially available (Aldrich, STREM) and were used as received.…”

Section: Methodsmentioning

confidence: 99%

Gold‐Catalyzed Hydroarylation of Alkynes

2003

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The hydroarylation of aryl‐substituted alkynes by substituted electron‐rich arenes is catalyzed by AuCl3 activated by such silver salts as AgSbF6. In the case of terminal alkynes, complete regioselectivity in favor of the 1,1‐disubstituted olefin is observed. In the case of electron‐poor alkynes such as acetylenecarboxylic acid ester, gold(I) complexes such as [Ph3PAuCl] activated by Ag salts or BF3·OEt2 are the best catalysts, resulting in opposite regioselectivity and high degrees of (Z)‐selectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Methodsmentioning

confidence: 99%

Gold‐Catalyzed Hydroarylation of Alkynes

2003

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“…Acetonitrile was freshly distilled from phosphorus pentoxide before use. Terminal alkynes [17] and diaryliodonium salts [18] were prepared according to the literature.…”

Section: Methodsmentioning

confidence: 99%

The cross-coupling reaction of vinylindiums generated via hydroindation of terminal alkynes with diaryliodoniums salts

Zhao

Yang

Wang

2006

Journal of Organometallic Chemistry

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“…Zwar ist eine direkte Substitution von X in 5 durch MeLi oder Cyclopentadienid nicht moglich: doch sind die aus 5 und Alkyllithium gebildeten nucleophilen Carbenoide 6 bei Temperaturen unterhalb -90" genugend stabil und lassen sich z. B. protonieren [17], alkylieren [l8], carbonylieren [ 191, carboxylieren [20], silylieren [21] oder thiomethylieren [22]. Demnach bieten sich die Reaktionsfolgen 6 + 7 -+ 1 bzw.…”

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“…Zur Abtrennung polymerer Verunreinigungen wird der dunkelbraune Ruckstand iiber 60 g Kieselgel chromatographiert. Durch Eluieren mit 1,Petrolather gewinnt man nach Abziehen des Lsgm 21. g bellgelbes 01, das bei 0" langsam fest wird und danach auch bei RT.…”

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Synthese von Triafulven‐Vorstufen aus trisubstituierten Cyclopropanen

Weber¹,

Sabbioni²,

Galli³

et al. 1988

Helvetica Chimica Acta

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Synthesis of Triafulvene-Precursors from Trisubstituted CyclopropauesTrisubstituted cyclopropanes 5a-f are prepared by carhene addition to the appropriate olefins. While 5a (Y = OAc) and 5c (Y = Cl) rearrange in the presence of BuLi, 5d (Y = SPh) is stable enough to allow the envisaged sequence for triafulvene (Scheme 2) : halogen-Li exchange, followed by methylation of 6d, gives 7d in a 93 YO yield; after base-induced elimination of HBr from 7d, the key precursor l-methylene-2-(phenylthio)cyclopropane (9, 70% yield) is isolated. Compound 9 is transformed into the corresponding sulfoxide 10 (83%), sulfone 11 (80%), and sulfonium fluorohorate 12 (95 % yield) by subsequent oxidation and methylation, respectively. Some 'H-NMR results of cyclopropanes 5a-f and 7d as well as of methylidene-cyclopropanes 9-11 are discussed.1. Einleitung. -Obwohl seit der Synthese der ersten substituierten Triafulvene und Calicene mehr als zwei Jahrzehnte vergangen sind, ist es bis heute nicht gelungen, den Grundkorper Calicen (2) zu isolieren, wahrend Triafulven (1) erst vor kurzem bei tiefer Temperatur spektroskopisch nachgewiesen worden ist [5] [6]. Die Schwierigkeiten bei der Synthese von 1 und 2 sind nicht nur auf ihre im Vergleich zu substituierten Vertretern geringere Stabilitat zuruckzufuhren. Sie beruhen auch darauf, dass sich viele Verfahren zur Synthese substituierter und elektronisch stabilisierter Triafulvene nicht auf die Grundkorper ubertragen lassen.

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Stereomutation in the Seyferth reaction

Cited by 13 publications

References 0 publications

Gold‐Catalyzed Hydroarylation of Alkynes

Gold‐Catalyzed Hydroarylation of Alkynes

The cross-coupling reaction of vinylindiums generated via hydroindation of terminal alkynes with diaryliodoniums salts

Synthese von Triafulven‐Vorstufen aus trisubstituierten Cyclopropanen

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