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Synthesis 2017; 49(09): 1983-1992
DOI: 10.1055/s-0036-1588376
DOI: 10.1055/s-0036-1588376
paper
Synthesis of 6,7-Dibromoflavone and Its Regioselective Diversification via Suzuki–Miyaura Reactions
Further Information
Publication History
Received: 23 October 2016
Accepted after revision: 20 November 2016
Publication Date:
10 January 2017 (online)
Dedicated to the memory of Prof. Tamás Patonay
Abstract
The first synthesis pathway to 6,7-dibromoflavone and its transformations to 7-aryl-6-bromo- and 6,7-diarylflavones by Suzuki–Miyaura reactions are presented. Due to the different electronic effects of bromo substituents, the first attack proceeded with good site selectivity at position 7.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588376.
- Supporting Information
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For reviews of site-selective palladium(0)-catalyzed cross coupling reactions, see:
For a simple guide for predicting the site selectivity of palladium-catalyzed cross-coupling reactions based on 1H NMR spectroscopic data of the nonhalogenated derivatives, see: