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The use of the free carboxylic acid of the methyl ester 4 a gave low yields of the coupling product (<10%), and the starting material could be recovered in>80% yield. Oxidative coupling with electron-rich substrates such as 2-naphthol, 3-phenanthrol, 9-phenanthrol, and 2-aminonaphthalene gave approximately 5-15% yield in all cases. Oxidation of electron-rich 2-naphthols to highly polar and colored byproducts was observed. For more details on possible oxidation products and their influence in oxidative coupling reactions
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The use of the free carboxylic acid of the methyl ester 4 a gave low yields of the coupling product (<10%), and the starting material could be recovered in>80% yield. Oxidative coupling with electron-rich substrates such as 2-naphthol, 3-phenanthrol, 9-phenanthrol, and 2-aminonaphthalene gave approximately 5-15% yield in all cases. Oxidation of electron-rich 2-naphthols to highly polar and colored byproducts was observed. For more details on possible oxidation products and their influence in oxidative coupling reactions, see: J. B. Hewgley, S.S. Stahl, M. C. Kozlowski, J. Am. Chem. Soc. 2008, 130, 12232-12233.
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70450152497
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See the Supporting Information for more information.
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See the Supporting Information for more information.
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70450124357
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note
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It was shown that it was necessary to have the ester in the 3-position for efficient coupling to occur because the reaction between 4a and 6i did not afford a mixed coupling product. In addition, 6i was reluctant to undergo homocoupling but could be reisolated in high yields, suggesting that the ester substituent in the 6-position is sufficiently electron-withdrawing to minimize the oxidation of 6i to unwanted byproducts. .
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