Anderson, David; Tortajada, Andreu; Hevia, Eva (2023). Highly Reactive Hydrocarbon Soluble Alkylsodium Reagents for Benzylic Aroylation of Toluenes using Weinreb Amides. Angewandte Chemie. International edition, 62(11), e202218498. Wiley 10.1002/anie.202218498
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Angew_Chem_Int_Ed_-_2023_-_Anderson_-_Highly_Reactive_Hydrocarbon_Soluble_Alkylsodium_Reagents_for_Benzylic_Aroylation_of.pdf - Accepted Version Available under License Publisher holds Copyright. Download (1MB) | Preview |
Deaggregating the alkyl sodium NaCH2SiMe3 with polydentate nitrogen ligands enables the preparation and characterisation of new, hydrocarbon soluble chelated alkylsodium reagents. Equipped with significantly enhanced metalating power over their organolithium counterparts, these systems can promote controlled sodiation of weakly acidic benzylic C-H bonds from a series of toluene derivatives under mild stoichiometric conditions. This has been demonstrated through the benzylic aroylation of toluenes with Weinreb amides, that delivers a wide range of 2-arylacetophenones in good to excellent yields. Success in isolating and determining the structures of key organometallic intermediates has provided useful mechanistic insight into these new sodium-mediated transformations.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Anderson, David Elliot, Tortajada Navarro, Andreu, Hevia Freire, Eva |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1521-3773 |
Publisher: |
Wiley |
Language: |
English |
Submitter: |
Pubmed Import |
Date Deposited: |
25 Jan 2023 13:59 |
Last Modified: |
15 Jan 2024 00:25 |
Publisher DOI: |
10.1002/anie.202218498 |
PubMed ID: |
36636916 |
Uncontrolled Keywords: |
aroylation coordination effects metalation organosodium structure/reactivity correlations |
BORIS DOI: |
10.48350/177392 |
URI: |
https://boris.unibe.ch/id/eprint/177392 |
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