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Pre‐Metalation Structural Insights into the Use of Alkali‐Metal‐Mediated Zincation for Directed ortho ‐Metalation of a Tertiary Aromatic Amide
Author(s) -
Clegg William,
Dale Sophie H.,
Hevia Eva,
Honeyman Gordon W.,
Mulvey Robert E.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503202
Subject(s) - metalation , zincate , amide , chemistry , alkali metal , medicinal chemistry , organic chemistry , zinc
The predator meets its prey in the structure of [{( i Pr) 2 NC(Ph)(O)}Li(μ‐tmp)(μ‐ t Bu)Zn( t Bu)] 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.