A substituted tricyclohexylphosphane with "conformational lock". Issue 23 (5th June 2020)

• Record Type: Journal Article
• Authors: Liu, Ziyue; Li, Tiejun; Zhao, Jianhong; Tang, Wenjun
• Is Part Of: Tetrahedron. Volume 76:Issue 23(2020)
• Publication Date: 2020-06-05
• Subjects: Tricyclohexylphosphane -- Conformational lock -- Ligand -- Cross-coupling -- Palladium; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131216
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A substituted tricyclohexylphosphane with "conformational lock", tri(4- trans -( tert -butyl)cyclohexyl)phosphane L, has been designed and synthesized. The ligand has shown similar steric bulkiness and conformations to tricyclohexylphosphane at solid state. The comparable or slightly better performance of ligand L compared to PCy3 in Suzuki-Miyaura coupling has demonstrated the similar steric properties of two ligands in reaction and the effectiveness of the chair conformer of the cyclohexyl rings. The ineffectiveness of both L and PCy3 in palladium-catalyzed aminations has also manifested the weakness of such ligands and a sterically more bulky ligand is needed in order to develop a more efficient amination. Graphical abstract: Image 1