Mixed Aggregates Containingn-Butyl-,sec-Butyl-, ortert-Butyllithium and a Chiral Lithium Amide Derived fromN-Isopropyl-O-methyl Valinol

1997 ◽  
Vol 119 (48) ◽  
pp. 11693-11694 ◽  
Author(s):  
Paul G. Williard ◽  
Chengzao Sun
Keyword(s):  
Lithium Amide ◽  
Mixed Aggregates

Structure of the Mixed Aggregates between a Chiral Lithium Amide and Phenyllithium or Vinyllithium

2012 ◽  
Vol 31 (13) ◽  
pp. 4801-4809 ◽  
Author(s):  
Hassan Oulyadi ◽  
Catherine Fressigné ◽  
Yi Yuan ◽  
Jacques Maddaluno ◽  
Anne Harrison-Marchand
Keyword(s):  
Lithium Amide ◽  
Mixed Aggregates

Probing solvent effects on mixed aggregates associating a chiral lithium amide and n-BuLi by NMR: from structure to reactivity

2014 ◽  
Vol 43 (38) ◽  
pp. 14219-14228 ◽  
Author(s):  
Gabriella Barozzino-Consiglio ◽  
Mathieu Rouen ◽  
Hassan Oulyadi ◽  
Anne Harrison-Marchand ◽  
Jacques Maddaluno
Keyword(s):  
Solvent Effects ◽  
Test Reaction ◽  
Lithium Amide ◽  
Mixed Aggregates

NMR shows a direct correlation between the concentration of a chiral lithium amide/n-BuLi complex and ees of a test reaction.

scholarly journals Lithium-mediated Ferration of Fluoroarenes

2020 ◽  
Vol 74 (11) ◽  
pp. 866-870
Author(s):  
Lewis C. H. Maddock ◽  
Alan Kennedy ◽  
Eva Hevia
Keyword(s):  
Hydrogen Atom ◽  
Organometallic Chemistry ◽  
Room Temperature ◽  
Structural Elucidation ◽  
Side Reactions ◽  
Metal Base ◽  
Lithium Amide ◽  
Mixed Metal ◽  
Important Challenge

While fluoroaryl fragments are ubiquitous in many pharmaceuticals, the deprotonation of fluoroarenes using organolithium bases constitutes an important challenge in polar organometallic chemistry. This has been widely attributed to the low stability of the in situ generated aryl lithium intermediates that even at –78 °C can undergo unwanted side reactions. Herein, pairing lithium amide LiHMDS (HMDS = N{SiMe3}2) with FeII(HMDS)2 enables the selective deprotonation at room temperature of pentafluorobenzene and 1,3,5-trifluorobenzene via the mixed-metal base [(dioxane)LiFe(HMDS)3] (1) (dioxane = 1,4-dioxane). Structural elucidation of the organometallic intermediates [(dioxane)Li(HMDS)2Fe(ArF)] (ArF = C6F5, 2; 1,3,5-F3-C6H2, 3) prior electrophilic interception demonstrates that these deprotonations are actually ferrations, with Fe occupying the position previously filled by a hydrogen atom. Notwithstanding, the presence of lithium is essential for the reactions to take place as Fe II (HMDS)2 on its own is completely inert towards the metallation of these substrates. Interestingly 2 and 3 are thermally stable and they do not undergo benzyne formation via LiF elimination.

scholarly journals Compositional flexibility in Li-N-H materials: implications for ammonia catalysis and hydrogen storage.

2021 ◽  
Author(s):  
Joshua Makepeace ◽  
Jake M Brittain ◽  
Alisha Sukhwani Manghnani ◽  
Claire Murray ◽  
Thomas J Wood ◽  
...  
Keyword(s):  
Energy Storage ◽  
Hydrogen Storage ◽  
Compositional Variation ◽  
Lithium Amide ◽  
Lithium Imide ◽  
Energy Storage Applications

Li-N-H materials, particularly lithium amide and lithium imide, have been explored for use in a variety of energy storage applications in recent years. Compositional variation within the parent lithium imide,...

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