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Lithium Diisopropylamide: Solution Kinetics and Implications for Organic Synthesis
Author(s) -
Collum David B.,
McNeil Anne J.,
Ramirez Antonio
Publication year - 2007
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.200603038
Subject(s) - lithium diisopropylamide , solvation , chemistry , kinetics , lithium (medication) , organic synthesis , context (archaeology) , reagent , solvent effects , organic reaction , lithium chloride , computational chemistry , organic chemistry , solvent , ion , catalysis , physics , psychology , paleontology , quantum mechanics , deprotonation , biology , psychiatry
Lithium diisopropylamide (LDA) is a prominent reagent used in organic synthesis. In this Review, rate studies of LDA‐mediated reactions are placed in the broader context of organic synthesis in three distinct segments. The first section provides a tutorial on solution kinetics, emphasizing the characteristic rate behavior caused by dominant solvation and aggregation effects. The second section summarizes substrate‐ and solvent‐dependent mechanisms that reveal basic principles of solvation and aggregation. The final section suggests how an understanding of mechanism might be combined with empirical methods to optimize yields, rates, and selectivities of organolithium reactions and applied to organic synthesis.