Article Synopsis
- Tris(bicyclo[1.1.1]pentyl)phosphine is a small tri-alkylphosphine created through radical addition of PH to [1.1.1]propellane, showing similar electron-donating power to PEt.
- This compound forms a reactive Pd(0) complex, Pd(PBcp), which is effective in catalyzing cross-coupling reactions involving sp electrophiles.
- Additionally, a reaction between [1.1.1]propellane and phenylphosphine yields the derivative PBcpPh, demonstrating the versatility of this synthetic method for bicyclopentylphosphines.
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Article Abstract
Tris(bicyclo[1.1.1]pentyl)phosphine can be prepared by radical addition of PH to [1.1.1]propellane, giving the smallest tri--alkylphosphine known. PBcp is substantially smaller than PCy and is comparable in electron-donating power to PEt. It gives a bis-ligated Pd(0) complex Pd(PBcp) that is exceptionally reactive toward alkyl halide oxidative addition and functions as a general ligand for palladium-catalyzed cross-coupling of sp electrophiles. Radical addition of [1.1.1]propellane to phenylphosphine gives the bis(bicyclo[1.1.1]pentyl)phosphine derivative PBcpPh, illustrating the generality of this approach to bicyclopentylphosphine synthesis.
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Tris(bicyclo[1.1.1]pentyl)phosphine: An Exceptionally Small Tri--alkylphosphine and Its Bis-Ligated Pd(0) Complex.
J Am Chem Soc
March 2023
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
Article Synopsis
- Tris(bicyclo[1.1.1]pentyl)phosphine is a small tri-alkylphosphine created through radical addition of PH to [1.1.1]propellane, showing similar electron-donating power to PEt.
- This compound forms a reactive Pd(0) complex, Pd(PBcp), which is effective in catalyzing cross-coupling reactions involving sp electrophiles.
- Additionally, a reaction between [1.1.1]propellane and phenylphosphine yields the derivative PBcpPh, demonstrating the versatility of this synthetic method for bicyclopentylphosphines.