Pre‐Metalation Structural Insights into the Use of Alkali‐Metal‐Mediated Zincation for Directed ortho‐Metalation of a Tertiary Aromatic Amide
W. Clegg, Sophie H. Dale, Eva Hevia, G.W. Honeyman, Robert E. Mulvey
Abstract
W. Clegg, Sophie H. Dale, Eva Hevia, G.W. Honeyman, Robert E. Mulvey
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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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.
Key concepts: Metalation, Zincate, Amide, Chemistry, Alkali metal, Medicinal chemistry, Organic chemistry, Zinc