Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide

Clegg, W and Dale, S H and Hevia, E and Honeyman, G W and Mulvey, R E (2006) Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide. Angewandte Chemie, 45 (15). pp. 2370-2374. ISSN 0044-8249 (https://doi.org/10.1002/anie.200503202)

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Abstract

The predator meets its prey in the structure of [{(iPr)2NC(Ph)(O)}Li(μ-tmp)(μ-tBu)Zn(tBu)] which reveals an aromatic amide–alkali metal zincate “precomplex” for directed ortho-metalation (DoM) that exists prior to the devouring (ortho-zincation) of the amide by the zincate. tmp=2,2,6,6-tetramethylpiperidide.

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