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• W3138251921 endingPage "4464" @default.
• W3138251921 startingPage "4451" @default.
• W3138251921 abstract "The donor–acceptor ability of frustrated Lewis pairs (FLPs) has led to widespread applications in organic synthesis. Single electron transfer from a donor Lewis base to an acceptor Lewis acid can generate a frustrated radical pair (FRP) depending on the substrate and energy required (thermal or photochemical) to promote an FLP into an FRP system. Herein, we report the Csp3–Csp cross-coupling reaction of aryl esters with terminal alkynes using the B(C6F5)3/Mes3P FLP. Significantly, when the 1-ethynyl-4-vinylbenzene substrate was employed, the exclusive formation of Csp3–Csp cross-coupled products was observed. However, when 1-ethynyl-2-vinylbenzene was employed, solvent-dependent site-selective Csp3–Csp or Csp3–Csp2 cross-coupling resulted. The nature of these reaction pathways and their selectivity has been investigated by extensive electron paramagnetic resonance (EPR) studies, kinetic studies, and density functional theory (DFT) calculations both to elucidate the mechanism of these coupling reactions and to explain the solvent-dependent site selectivity." @default.
• W3138251921 created "2021-03-29" @default.
• W3138251921 creator A5005757075 @default.
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• W3138251921 creator A5085085833 @default.
• W3138251921 date "2021-03-15" @default.
• W3138251921 modified "2023-10-17" @default.
• W3138251921 title "Site-Selective C_sp³–C_sp/C_sp³–C_sp² Cross-Coupling Reactions Using Frustrated Lewis Pairs" @default.
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• W3138251921 doi "https://doi.org/10.1021/jacs.1c01622" @default.
• W3138251921 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8041292" @default.
• W3138251921 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33719443" @default.
• W3138251921 hasPublicationYear "2021" @default.
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