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Organolithium reagent

Organolithium reagents are a collection of organolithium compounds that are widely used in organic synthesis and polymer chemistry. These reagents are used to transfer the organic group or the lithium atom to diverse substrates, usually through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for…

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Overview

History and development

Structure

Reactivity and applications

Organolithium reagents in asymmetric synthesis

Preparation

Handling

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Organolithium reagent

Nodes109
Edges108
Triples134
Avg. degree1.98
Density0.018349
Components1

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Organolithium reagent

Top relations

related to Structure and reactivity · 17
Organolithium reagent → Also, As, For, HMPA, However, In, It, LDA, LDA-mediated, Lewis, LiHMDS, One, The, THF, Thus, TMEDA, Toward
related to Solution structure · 15
Organolithium reagent → Et2O, For, HMPA, It, Lewis, Li, LiBu-n, Methyllithium, NMR, On, Organolithium, Phenyllithium, Separate NMR, THF, TMEDA
related to As base · 13
Organolithium reagent → As, Butyllithium, LDA, LiHMDS, LiNR2, Lithium, NH, OH, Organolithium, Reagents, SH, Some, The
related to Transmetalation · 11
Organolithium reagent → Bu3Sn, BuLi, Common, In, Li/Hg, Li/Sn, Li/Te, Organocopper, Organolithium, The, This
related to Nature of carbon–lithium bond · 9
Organolithium reagent → Due, For, However, Li, One, Owing, The, These, While
related to history · 7
Organolithium reagent → Georg Wittig, Grignard, Henry Gilman, In, Karl Ziegler, Since, Studies
related to Organolithium reagents in asymmetric synthesis · 7
Organolithium reagent → Asymmetric, Chiral, In, N-Boc-N-benzylamine, The, They, Transmetalation
related to Metalation · 6
Organolithium reagent → For, In, Metalation, Some, The, This
has application · 5
Organolithium reagent → As, Li, Some, The, Thus
related to Handling · 5
Organolithium reagent → Alkyllithium, Organolithium, Reactions, The, They

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Important terminology

reagents organolithium lithium species used often addition also compounds metalation alkyllithium reaction common reactions exchange form bond reactivity example ligands

Entity relationships Subject–Predicate–Object triples

SubjectPredicateObjectConfidenceSrc
solubility in nonpolar solvents that complicate the issueinstance ofcertain organolithium compounds possess properties0.80text
THFinstance ofmost silyllithiums tend to form monomeric structures coordinated with solvent molecules0.80text
and only a few silyllithiums have been characterized as higher aggregatesinstance ofmost silyllithiums tend to form monomeric structures coordinated with solvent molecules0.80text
tetrahydrofuraninstance ofSeparate NMR signals can also differentiate the presence of multiple aggregates from a common monomeric unit.Organolithium compounds bind Lewis bases0.80text
monomers are more reactive in alkyllithiumsinstance ofIt was originally proposed that lower aggregates0.80text
LDAinstance ofand for lithium amides0.80text
dimer-based reactions are commoninstance ofand for lithium amides0.80text
LiHMDSinstance ofThe addition of HMPA to lithium amides0.80text
LDA often results in a mixture of dimer/monomer aggregates in THFinstance ofThe addition of HMPA to lithium amides0.80text
LiClO4 can improve the stereoselectivity of the reaction.When the ketone is sterically hinderedinstance ofAddition of lithium salts0.80text
using Grignard reagents often leads to reduction of the carbonyl group instead of additioninstance ofAddition of lithium salts0.80text
radical reactions or metalinstance oftheir use is still limited due to competing side reactions0.80text

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