Unveiling the Significance of tert-Butoxides in Transition Metal-Free Cross-Coupling Reactions.
Tert-butoxides
Cross-coupling
Radical anions
Single electron transfer
Transition metal-free
Journal
Topics in current chemistry (Cham)
ISSN: 2364-8961
Titre abrégé: Top Curr Chem (Cham)
Pays: Switzerland
ID NLM: 101691301
Informations de publication
Date de publication:
11 Oct 2024
11 Oct 2024
Historique:
received:
30
12
2023
accepted:
21
09
2024
medline:
12
10
2024
pubmed:
12
10
2024
entrez:
11
10
2024
Statut:
epublish
Résumé
The astounding reactivity of tert-butoxides in transition metal-free coupling reactions is driving the scientific community towards a new era of environmental friendly, as well as cost-effective, transformation strategies. Transition metal-catalyzed coupling reactions generate hazardous wastes and require harsh reaction conditions, mostly at elevated temperature, which increases not only costs but also environmental concerns regarding the methodology. Tert-butoxide-catalyzed/mediated coupling reactions have several advantages and potential applications. They can form carbon-carbon, carbon-heteroatom, and heteroatom-heteroatom bonds under mild reaction conditions. Mechanistic insights into these reactions include both ionic and radical pathways, with the fate of the intermediates depending on the reaction conditions and/or additives used in the reactions. Among all of the known tert-butoxides, potassium tert-butoxide has pronounced applications in transition metal-free coupling reactions as compared to other tert-butoxides, such as sodium and lithium tert-butoxides, because of the higher electropositivity of potassium compared to sodium and lithium. Moreover, potassium tert-butoxide can act as a source of base, nucleophile and single electron donors in various important transformations. In this review, we provide an extensive overview and complete compilation of transition metal-free cross-coupling reactions catalyzed/promoted by tert-butoxides during the past 10 years.
Identifiants
pubmed: 39394383
doi: 10.1007/s41061-024-00478-5
pii: 10.1007/s41061-024-00478-5
doi:
Substances chimiques
Transition Elements
0
Butanols
0
tert-butoxide, potassium
865-47-4
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
32Subventions
Organisme : DST-SERB INDIA
ID : CRG/2019/002333
Organisme : DST-SERB INDIA
ID : CRG/2019/002333
Organisme : CSTUP
ID : Project-1818
Organisme : CSTUP
ID : Project-1818
Informations de copyright
© 2024. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
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