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Lookup NU author(s): Dr Nathan Davison, Dr Paul Waddell, Dr Corinne Wills, Dr Casey Dixon, Dr Erli Lu
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).
© 2023 The Authors. Published by American Chemical Society.Organosodium chemistry is underdeveloped compared with organolithium chemistry, and all the reported organosodium complexes exhibit similar, if not identical, reactivity patterns to their lithium counterparts. Herein, we report a rare organosodium monomeric complex, namely, [Na(CH2SiMe3)(Me6Tren)] (1-Na) (Me6Tren: tris[2-(dimethylamino)ethyl]amine) stabilized by a tetra-dentate neutral amine ligand Me6Tren. Employing organo-carbonyl substrates (ketones, aldehydes, amides, ester), we demonstrated that 1-Na features distinct reactivity patterns compared with its lithium counterpart, [Li(CH2SiMe3)(Me6Tren)] (1-Li). Based on this knowledge, we further developed a ligand-catalysis strategy to conduct ketone/aldehyde methylenations, using [NaCH2SiMe3]∞ as the CH2 feedstock, replacing the widely used but hazardous/expensive C═O methylenation methods, such as Wittig, Tebbe, Julia/Julia-Kocieński, Peterson, and so on.
Author(s): Davison N, McMullin CL, Zhang L, Hu S-X, Waddell PG, Wills C, Dixon C, Lu E
Publication type: Article
Publication status: Published
Journal: Journal of the American Chemical Society
Year: 2023
Volume: 145
Issue: 11
Pages: 6562–6576
Print publication date: 22/03/2023
Online publication date: 08/03/2023
Acceptance date: 30/01/2023
Date deposited: 28/03/2023
ISSN (print): 0002-7863
ISSN (electronic): 1520-5126
Publisher: American Chemical Society
URL: https://doi.org/10.1021/jacs.3c01033
DOI: 10.1021/jacs.3c01033
PubMed id: 36890641
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