Issue in Honor of Prof. Lutz F. Tietze ARKIVOC 2007 (v) 6-19
Gold-catalyzed reactions of oxo-alkynes Nitin T. Patil and Yoshinori Yamamoto*
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan E-mail: yoshi@mail.tains.tohoku.ac.jp
Dedicated to Professor Lutz Tietze on the occasion of his 65th Birthday
Abstract
Gold (I) and gold (III) complexes show unique catalytic activities toward alkynes; both inter and intramolecular addition of nucleophiles to alkynes is promoted in the presence of gold catalysts. This review focuses on the gold catalyzed reactions of alkynes tethered with carbonyl groups along with their interesting mechanistic aspects.
Keywords: Gold catalysis, alkynals, alkynones, domino reactions
Introduction
The formation of C-C and C-X bonds by the use of transition metal catalysts is one of the most interesting and intriguing subjects in organic chemistry. The formation of these bonds by using various transition metals such as Pd, Ni, Ru, Rh has been extensively investigated and documented in the literature.1 The catalysis of organic reactions by gold compounds has recently been shown to be a powerful tool in organic synthesis.2 This chemistry is also valuable in constructing complex molecules. Although gold is considered as an expensive metal, the unique catalytic properties exhibited by the various gold complexes have encouraged organic chemists to explore the viability of these complexes as catalysts. Likewise other transition metals, gold salts are capable of forming several bonds in one pot, without isolating any intermediates, commonly referred as domino3 or tandem reactions. It is obvious that this type of reactions would allow the minimization of waste elements and most importantly the reaction can be performed with high atom economy.4 Over the decades the usefulness of gold catalyst has been realized and has drawn the attention of numerous research groups, which has been reflected in a number of research publications in the literature. Cationic gold (I) and gold (III) show unique activities toward alkynes, promoting the nucleophilic addition of a variety of functional groups both inter- and intramolecularly. As a part of continuing interest on gold catalysis, we were
ISSN 1424-6376 Page 6 ©ARKAT
0
