Unveiling the Significance of tert-Butoxides in Transition Metal-Free Cross-Coupling Reactions.

Autor: Kumar V; Amity Institute of Click Chemistry Research and Studies, Amity University, Noida, India.; CSIR-Central Drug Research Institute, Lucknow, India., Majee S; Amity Institute of Click Chemistry Research and Studies, Amity University, Noida, India.; Amity Institute of Biotechnology, Amity University, Noida, India., Anjali K; Amity Institute of Click Chemistry Research and Studies, Amity University, Noida, India.; Amity Institute of Biotechnology, Amity University, Noida, India., Saha B; Amity Institute of Biotechnology, Amity University, Noida, India. bsaha1@amity.edu., Ray D; Amity Institute of Click Chemistry Research and Studies, Amity University, Noida, India. dray@amity.edu.; Amity Institute of Biotechnology, Amity University, Noida, India. dray@amity.edu.
Jazyk: angličtina
Zdroj: Topics in current chemistry (Cham) [Top Curr Chem (Cham)] 2024 Oct 11; Vol. 382 (4), pp. 32. Date of Electronic Publication: 2024 Oct 11.
DOI: 10.1007/s41061-024-00478-5
Abstrakt: 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.
(© 2024. The Author(s), under exclusive licence to Springer Nature Switzerland AG.)
Databáze: MEDLINE
Externí odkaz: