Fulvene Synthesis by Rhodium(I)‐Catalyzed [2+2+1] Cycloaddition: Synthesis and Catalytic Activity of Tunable Cyclopentadienyl Rhodium(III) Complexes with Pendant Amides

It has been established that a RhI+/segphos complex catalyzes the [2+2+1] cycloaddition of 1,6‐diynes with cyclopropylideneacetamides to give substituted fulvenes in good yields. The reductive complexation of the product fulvenes with RhCl3 in EtOH furnished the corresponding dinuclear cyclopentadie...

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Published inAngewandte Chemie Vol. 129; no. 13; pp. 3644 - 3647
Main Authors Yoshizaki, Soichi, Shibata, Yu, Tanaka, Ken
Format Journal Article
LanguageEnglish
German
Published Weinheim Wiley Subscription Services, Inc 20.03.2017
Subjects
Amides
Anellierungen
Bearing
C-H-Funktionalisierung
Catalysts
Catalytic activity
Chemical reactions
Chemical synthesis
Chemistry
Complexation
Cycloaddition
Cyclopentadienylkomplexe
Fulvene
Organic chemistry
Rhodium
Synthesis (chemistry)
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Summary:It has been established that a RhI+/segphos complex catalyzes the [2+2+1] cycloaddition of 1,6‐diynes with cyclopropylideneacetamides to give substituted fulvenes in good yields. The reductive complexation of the product fulvenes with RhCl3 in EtOH furnished the corresponding dinuclear cyclopentadienyl RhIII complexes bearing a pendant amide moiety. These RhIII complexes were highly active catalysts for oxidative annulation and cyclization through C(sp2)−H and C(sp3)−H functionalization. Ful‐minante Reaktion: Ein RhI+/segphos‐Komplex katalysiert die [2+2+1]‐Cycloaddition von 1,6‐Diinen mit Cyclopropylidenacetamiden zur Bildung von substituierten Fulvenen. Die reduktive Komplexierung dieser Produkte mit RhCl3 in EtOH liefert die entsprechenden zweikernigen Cyclopentadienyl‐RhIII‐Komplexe (siehe Schema), die hoch aktive Katalysatoren für oxidative Anellierungen und Cyclisierungen über C(sp2)‐H‐ und C(sp3)‐H‐Funktionalisierungen sind.
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201612590