Alkali-Metal-Mediated Zincation of Ferrocene: Synthesis, Structure, and Reactivity of a Lithium Tmp/Zincate Reagent

✍ Scribed by Helen R. L. Barley; William Clegg; Sophie H. Dale; Eva Hevia; Gordon W. Honeyman; Alan R. Kennedy; Robert E. Mulvey

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 123 KB
• Volume: 117
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200501560

✦ Synopsis

Lithium dialkyl tetramethylpiperidino zincates of the general formula "[LiR 2 Zn(tmp)]" (tmp = 2,2,6,6-tetramethylpiperidine) represent an important subfamily of organozincate reagent. Established only in 1999 through the pioneering work on "[LitBu 2 Zn(tmp)]" by Kondo et al., [1] "tmp zincates" have found application as highly chemo-and/or regioselective bases for the metalation of alkyl benzoates and related aza aromatic compounds, bromopyridines, and various halobenzenes. [2,3] Recent reports [4] have highlighted the poverty of structural information available on lithium zincates in general. Tmp zincates are no exception in this regard, with a 13 C NMR spectroscopic study of "[LitBu 2 Zn(tmp)]" in solution [1] providing the only morsel of structural evidence