Specificity is of the utmost importance in organic reactions. Using our developed protocol of �deficiency catalysis� involving promoted hydrocarbon media (Organometallics, 2013), a number of aryl substrates which offer competing sites of metalation have been made to undergo a focused, i.e., a regiospecific metalation. Among these aryl substrates are the methoxynaphthalenes and the methylanisoles. For 1-methoxynaphthalenes, the �focused� site of metalation is the 2-position while for the 3-methylanisole it is the 6-position.Each �focused� metalation has been realized in predominance greater than 10:1. Similar results have been observed for 2-methyoxynaphthalene (3-lithiation) and 2- methylanisole (6-metalation). A number of derivatives of each of these systems have been isolated and characterized.

New "deficiency catalyzed" hydrocarbon media aryl metalations

246th National Meeting (2013)

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