Ein Eldorado für die homogene Katalyse?

Abstract

Der Lockruf des Goldes ertönt nicht nur in den Büchern Jack Londons, auch in den Labors der Katalyseforschung kann es zu einem Goldrausch kommen. Mit hoher katalytischer Aktivität ermöglichen Goldsalze Dominokupplungsreaktionen unter C‐Heteroatom‐ und C‐C‐Verknüpfung. So sind furylsubstituierte Produkte 2 präparativ einstufig aus jeweils drei Einheiten Allenylketon 1 herstellbar.

Gold Catalysis: Domino Reaction of En‐Diynes to Highly Substituted Phenols

“…In the field of homogeneous catalysis with transition metals, the role of gold catalysts has emerged from a curiosity to a common tool, which now is used by many groups for a diverse field of newly developed organic transformations. [1] Most of these reactions can be performed under remarkably mild conditions and with high atom efficiency. Among other reactions, our group contributed the furan-yne cyclization, which proved to be a versatile tool for the generation of a wide array of important heterocyclic systems (Scheme 1).…”

Gold(I)‐Catalyzed Formation of Benzo[b]furans from 3‐Silyloxy‐1,5‐enynes

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Gold-catalyzed [1] cyclizations of aromatic and heteroaromatic compounds with alkynes offer new ways for the efficient construction of bioactive compounds, and have attracted much attention in the last decade.Recently, Kirsch et al [2] developed an interesting method for the synthesis of bicyclic formyl compounds. It is based on the cyclization of 3-silyloxy-1,5-enynes under mild conditions with gold(I) catalysts and iPrOH as an additive in a process that involves a 6-endo-dig cyclization to the distal position of the double bond and a pinacol rearrangement (Scheme 1).

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“…Gold-catalyzed [1] cyclizations of aromatic and heteroaromatic compounds with alkynes offer new ways for the efficient construction of bioactive compounds, and have attracted much attention in the last decade.…”

Theoretical study of the reaction of alkynes with furan catalyzed by AuCl3 and AuCl

“…Gold catalysis is still rare in organic synthesis, but it appears to offer new possibilities for regioselectivity 2, 4–8 (for highlights of the goal application, see Ref. 9). The first intramolecular reaction of furan with alkynes catalyzed by AuCl 3 to yield phenol was obtained by Hashmi and colleagues 4, 8 (Scheme ).…”