Abstract
A general synthetic approach to various catechol derivatives was developed using a copper-catalyzed cross-coupling reaction of 1,2-dimethoxy-4-brornomethyl, 1-ethoxy-2-methoxy-4-bromomethyl- and 2-ethoxy-1-methoxy-4-bromomethylbenzenes with Grignard reagents. Dilithium tetrachlorocuprate was an acceptable catalyst in the dimethoxy series, whereas copper(I) iodide in THF-HMPA was a superior catalyst in all cases due to decreased side reactions, i.e., reduction and reductive coupling. Methyl-substituted analogs of methyl eugenol, a potent attractant of Oriental fruit fly,Dacus dorsalis Hendel, were synthesized by this method and evaluated for attractancy in field tests.
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On leave from the Institute of Organic Chemistry of the Armenian Academy of Sciences, Yerevan, Armenia; author to whom correspondence should be addressed.
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Khrimian, A.P., DeMilo, A.B., Waters, R.M. et al. Synthesis of attractants for oriental fruit flyDacus dorsalis Hendel using a catalytic organocopper coupling reaction. J Chem Ecol 19, 2935–2946 (1993). https://doi.org/10.1007/BF00980593
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DOI: https://doi.org/10.1007/BF00980593