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2009•Journal of the American Chemical SocietyOpen access

Ligand-Controlled Access to [4 + 2] and [4 + 3] Cycloadditions in Gold-Catalyzed Reactions of Allene-Dienes

Pablo Mauleón, Rachel M. Zeldin, Ana Z. González, F. Dean Toste

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Abstract

By adjustment of the electronic properties of the ancilliary ligands, high selectivity can be achieved for either [4 + 2] or [4 + 3] cycloaddition reactions of allene-dienes catalyzed by gold(I). Triarylphosphitegold(I) complexes are employed as catalysts for a [4 + 2] cycloaddition reaction leading to alkylidenecyclohexenes. Conversely, di-tert-butylbiphenylphosphinegold(I)-catalyzed reactions afford cycloheptadienes via [4 + 3] cycloaddition reactions.

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What this paper is about

By adjustment of the electronic properties of the ancilliary ligands, high selectivity can be achieved for either [4 + 2] or [4 + 3] cycloaddition reactions of allene-dienes catalyzed by gold(I). Triarylphosphitegold(I) complexes are employed as catalysts for a [4 + 2] cycloaddition reaction leading to alkylidenecyclohexenes. Conversely, di-tert-butylbiphenylphosphinegold(I)-catalyzed reactions afford cycloheptadienes via [4 + 3] cycloaddition reactions.

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Available abstract

By adjustment of the electronic properties of the ancilliary ligands, high selectivity can be achieved for either [4 + 2] or [4 + 3] cycloaddition reactions of allene-dienes catalyzed by gold(I). Triarylphosphitegold(I) complexes are employed as catalysts for a [4 + 2] cycloaddition reaction leading to alkylidenecyclohexenes. Conversely, di-tert-butylbiphenylphosphinegold(I)-catalyzed reactions afford cycloheptadienes via [4 + 3] cycloaddition reactions.

Key concepts: Cycloaddition, Allene, Chemistry, Catalysis, Selectivity, Ligand (biochemistry), Combinatorial chemistry, Photochemistry

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