Concepedia

Gold-Catalyzed Annulation/Fragmentation: Formation of Free Gold Carbenes by Retro-Cyclopropanation

César R. Solorio‐Alvarado, Antonio M. Echavarren

Journal of the American Chemical Society · 2010 · 118 citations · 23 references

DOI

Concepts

Abstract

The gold(I)-catalyzed cyclization of 1-(prop-2-yn-1-yl)-2-alkenylbenzenes substituted at the benzylic position with OR groups gives 1,3-disubstituted naphthalenes with concomitant fragmentation of the alkene. One of these annulations proceeds by a retro-cyclopropanation that leads to free gold(I) carbenes.

References

23

Cycloisomerization of 1,<i>n</i>‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Véronique Michelet, Patrick Y. Toullec, Jean‐Pierre Genêt · Angewandte Chemie International Edition · 2008 · 984 citations

, , +10

Platinum- and Gold-Catalyzed Cycloisomerization Reactions of Hydroxylated Enynes

Victor Mamane, Tobias Gress, Helga Krause et al. · Journal of the American Chemical Society · 2004 · 544 citations

, , +11

A Gold Catalyst for Carbene‐Transfer Reactions from Ethyl Diazoacetate

Manuel R. Fructos, Tomás R. Belderraín, Pierre de Frémont et al. · Angewandte Chemie International Edition · 2005 · 452 citations

, , +10

DFT Study of the Mechanisms of In Water Au(I)-Catalyzed Tandem [3,3]-Rearrangement/Nazarov Reaction/[1,2]-Hydrogen Shift of Enynyl Acetates:  A Proton-Transport Catalysis Strategy in the Water-Catalyzed [1,2]-Hydrogen Shift

Fuqiang Shi, Xin Li, Yuanzhi Xia et al. · Journal of the American Chemical Society · 2007 · 302 citations

, , +13

Construction of Heterocyclesby the Strategic Use of Alkyne π-Activation in CatalyzedCascade Reactions

Stefan F. Kirsch · Synthesis · 2008 · 278 citations

, , +16