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Synthesis 2013; 45(9): 1227-1234
DOI: 10.1055/s-0032-1318454
DOI: 10.1055/s-0032-1318454
paper
Gold-Catalyzed Benzannulation of Electronically Rich/Rich and Deficient/Deficient Oxoalkynes with Alkynes
Further Information
Publication History
Received: 10 January 2013
Accepted after revision: 20 February 2013
Publication Date:
04 April 2013 (online)
Abstract
Two different strategies have been developed to perform the gold-catalyzed benzannulation of both electron-rich pyridine containing oxoalkynes with electron-rich alkynes as well as electron-deficient pyridine containing oxoalkynes with electron-deficient alkynes. The benzannulation between electron-rich oxoalkynes with electron-rich alkynes proceeds in the presence of highly electron-deficient gold catalysts, whereas using catalytic amount of alcohol benzannulation was performed efficiently between electron-deficient oxoalkynes with electron-deficient alkynes.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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Selected review articles on gold catalysis:
We cannot rule out the possibility of silver effect on gold catalysis, as sometimes combination of gold salts with silver salts leads to the formation of bimetallic clusters, see:
For a successful utilization of alkynes with strong donor ligands, see:
For observation of product inhibition by nitrogen-containing, potentially chelating reaction products, see:
So far this has been avoided by using gold(I), which has a low affinity to nitrogen ligands, see: