Dicobalt Octacarbonyl Catalyzed Carbonylated Cycloaddition of Triynes to Functionalized Tetracycles

Abstract

[reaction: see text]. We have demonstrated that a dicobalt octacarbonyl catalyzed double [2 + 2 + 1] carbonylative cycloaddition reaction of triyne can be carried out to yield a novel 5.5.5.6 tetracyclic di-enone system.

Carbon Flatland: Planar Tetracoordinate Carbon and Fenestranes

“…In view of the successful synthesis of fenestranes from readily available di-enynes of type 207 and the tandem PK reactions of 204b − d , Chung et al surmised that triynes of type 208 might also lead to fenestranes via PK reactions …”

Construction of Fused Tropone Systems Through Intramolecular Rh(I)-Catalyzed Carbonylative [2+2+2+1] Cycloadditon of Triynes

“…Inter- and intramolecular alkyne cyclotrimerizations with various transition metal complexes furnished wide varieties of polysubstituted benzene derivatives (Saito and Yamamoto, 2000 ; Kotha et al, 2005 ; Chopade and Louie, 2006 ). When the cycloaddition of alkynes carried out under carbon monoxide atmosphere, a range of interesting carbonylative cycloaddition products were observed instead of benzene formation (Scheme 1 ) (Gesing et al, 1980 ; Badrieh et al, 1994 ; Son et al, 2000a , b , 2001 ; Shibata et al, 2001 , 2002 ; Sugihara et al, 2001 ; Huang and Hua, 2007 ).…”

Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

“…31,32 Ruthenium and cobalt are other metals that are associated with carbonylative cycloaddition reactions, but control experiusing their carbonyl complexes gave low to no conversion (entries 10 and 11). 33,34 Noteworthy, we observed during this study that the triyne substrates 1 are poorly stable and needed to be freshly purified prior to cycloaddition experiments to avoid yield depletion.…”