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Updated: May 2, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Structural effects in lithiocuprate chemistry: the elucidation of reactive pentametallic complexes
Philip J Harford1, Andrew J Peel, Joseph P Taylor
1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK).
Abstract:
TMPLi (TMP=2,2,6,6-tetramethylpiperidide) reacts with Cu(I) salts in the presence of Et2O to give the dimers [{(TMP)2Cu(X)Li2 (OEt2)}2] (X=CN, halide). In contrast, the use of DMPLi (DMP=cis-2,6-dimethylpiperidide) gives an unprecedented structural motif; [{(DMP)2CuLi(OEt2)}2LiX] (X=halide). This formulation suggests a hitherto unexplored route to the in situ formation of Gilman-type bases that are of proven reactivity in directed ortho cupration.
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