Survival of substituents is a reoccurring problem in metalation chemistry. In particular, the halogens, -Br and �I, are prone to undergo the halogen/metal exchange when ortho-lithiations are attempted. We have developed a strategy whereby both p-Br and p-I substituents are preserved upon metalation, viz,      By use of ortho-lithiodimethylbenzylamine (o- LiDMBA), a novel metalating agent, such lithiations can be accomplished. o- LiDMBA can be easily prepared by our �deficiency catalysis� procedure which features a doped hydrocarbon medium and n-BuLi (Organometallics, 2013). The activity of the generated metalating agent is diminished by the transfer thereby providing a more focused metalation system. Derivatives of several of these systems have been isolated and characterized.

Transfer metalation, a new metalation methodology

246th National Meeting (2013)

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