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Three-Component Cyclobutylation via Silver(I)-Catalyzed Carbene Transfer Reactions with [1.1.1]Propellane

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Title
Three-Component Cyclobutylation via Silver(I)-Catalyzed Carbene Transfer Reactions with [1.1.1]Propellane
Author(s)
Sanghoon Shin; Yuhyun Kim; Sungwoo Hong
Publication Date
2023-10
Journal
ACS CATALYSIS, v.13, no.20, pp.13325 - 13332
Publisher
AMER CHEMICAL SOC
Abstract
In this study, we report an innovative Ag(I)-catalyzed carbene transfer reaction that employs [1.1.1]propellane as a precursor to form the methylene cyclobutyl carbene complex for a controllable three-component reaction. The key strategy of this method involves the formation of Ag-bound oxonium ions as intermediates, which are generated by the reaction between the Ag-carbene complex and cyclic ether-type solvents such as THF and 1,4-dioxane. The subsequent nucleophile-induced C-O bond cleavage leads to a three-component etherification of methylene cyclobutane. Employing this strategy, we successfully coupled various amine and alcohol partners, demonstrating the method's potential for the late-stage functionalization of intricate, biologically relevant molecules and synthetic manipulations of the resulting products. To further explore the mechanism driving selective three-component reactions, we have conducted comprehensive experimental and computational studies.
URI
https://pr.ibs.re.kr/handle/8788114/14022
DOI
10.1021/acscatal.3c03681
ISSN
2155-5435
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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