Ir and Rh complex-catalyzed intramolecular alkyne–alkyne couplings with carbon monoxide and isocyanides

Intramolecular [2+2+1] cycloaddition of diynes with carbon monoxide was catalyzed by Vaska's complex (IrCl(CO)(PPh 3) 2) or IrCl(cod)(dppp), and cyclopentadienones were obtained in good to high yields. The first catalytic synthesis of iminocyclopentadienes was achieved by portionwise additions...

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Published inTetrahedron Vol. 58; no. 43; pp. 8661 - 8667
Main Authors Shibata, Takanori, Yamashita, Koji, Katayama, Emi, Takagi, Kentaro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.10.2002
Elsevier
Subjects
alkynes
carbonylations
Chemistry
Chemistry, Organic
coupling reactions
diynes
iridium
Physical Sciences
rhodium
Science & Technology
iridium
diynes
carbonylations
alkynes
coupling reactions
rhodium
PAUSON-KHAND REACTION
ORGANIC-SYNTHESIS
METAL-DIENE COMPLEXES
PERISELECTIVITY
PROMOTED CYCLOCARBONYLATION
MEDIATED 2+2+1 CYCLOADDITIONS
CYCLOPENTADIENONES
ALPHA,OMEGA-DIYNES
CYCLIZATION
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Summary:Intramolecular [2+2+1] cycloaddition of diynes with carbon monoxide was catalyzed by Vaska's complex (IrCl(CO)(PPh 3) 2) or IrCl(cod)(dppp), and cyclopentadienones were obtained in good to high yields. The first catalytic synthesis of iminocyclopentadienes was achieved by portionwise additions of isocyanides to a solution of diynes and Rh catalyst ([RhCl(cod)] 2). Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01122-5