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Synlett 2013; 24(4): 412-423
DOI: 10.1055/s-0032-1317944
DOI: 10.1055/s-0032-1317944
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Regioselective Suzuki–Miyaura Reactions of Aromatic Bis-triflates: Electronic versus Steric Effects
Further Information
Publication History
Received: 09 October 2012
Accepted after revision: 04 December 2012
Publication Date:
11 January 2013 (online)
Dedicated to Professor Dr. Viqar Uddin Ahmad on his 72th birthday
Abstract
Suzuki–Miyaura reactions of aromatic bis-triflates, readily available from the corresponding hydroxylated arenes, often proceed with excellent regioselectivity and provide a convenient approach to various arylated benzene derivatives, such as biphenyls, terphenyls, and arylated benzophenones, naphthalenes, xanthones, flavones, coumarins, anthraquinones, tetralones, and fluorenones. The regioselectivity is controlled by steric and electronic parameters and strongly depends on the structure of the substrates.
1 Introduction
2 Benzoates, Phthalates, and Naphthoates
3 Benzophenones and Diphenyl Sulfones
4 Xanthones and Thioxanthones
5 Flavones and Coumarins
6 Anthraquinones, Tetralones, and Fluorenones
7 Conclusion
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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: