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Naphthaleneor DTBB-catalyzed lithiation of chloroimines 1, deprotonated chlorobenzyl alcohols, mercaptanes or amines 4, and 3-phenylthiopropylamine 7 in THF at -78deg.C leads to the formation of the corresponding intermediates 2, 5 and 8, which by reaction with carbonyl compounds as electrophiles afford the expected bifunctionalized compounds 3, 6 and 9, respectively.

Functionalized Organolithium Compounds Through an Arene-Catalyzed Lithiation