ChemInform Abstract: Cationic Rhodium(I)/H8-binap Complex Catalyzed [2 + 2 + 2] Cycloadditions of 1,6- and 1,7-Diynes with Carbonyl Compounds

Autor:	Ken Tanaka, Rie Tanaka, Yousuke Otake
Rok vydání:	2009
Předmět:	Ligand Stereochemistry Cationic polymerization chemistry.chemical_element General Medicine Medicinal chemistry Phosphonate Catalysis Rhodium chemistry.chemical_compound chemistry Reactivity (chemistry) Bifunctional BINAP
Zdroj:	ChemInform. 40
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200942021
Popis:	We have established that a cationic rhodium(I)/H8-binap complex catalyzes [2+2+2] cycloadditions of a variety of 1,6- and 1,7-diynes with both electron-deficient and electron-rich carbonyl compounds, leading to dienones in high yield under mild reaction conditions. In the reactions with acyl phosphonates, the reactivity of 1,6- and 1,7-diynes was highly dependent on their own structures. The addition of chelating diethyl oxalate effectively promoted the [2+2+2] cycloadditions involving acyl phosphonates, presumably due to the equilibrium formation of the desired 1:1 rhodium complex of the diyne and the acyl phosphonate by facile ligand exchange between the diyne and weakly coordinated diethyl oxalate. In the reactions involving bifunctional carbonyl compounds or unsymmetrical 1,6-diynes, high chemo- or regioselectivities were observed.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Databáze:	OpenAIRE
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