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Phosphine–phosphite ligands in the palladium-catalyzed asymmetric allylic alkylation: Electronic and steric effects

Paper ID Volume ID Publish Year Pages File Format Full-Text
50019 46776 2013 4 PDF Available
Title
Phosphine–phosphite ligands in the palladium-catalyzed asymmetric allylic alkylation: Electronic and steric effects
Abstract

•Phosphine–phosphite ligands with different tether lengths were tested in asymmetric allylation.•The reaction rate and enantioselectivity were strongly sensitive to the chain length.•A steady relationship was observed between the ligands' basicity and their catalytic activity.•The role of the biaryl terminal moiety and the stereogenic elements in the backbone was also studied (ees up to 74%).•Alkylene carbonates were successfully used as green solvents for the catalytic reaction (ees up to 69%).

The asymmetric allylic alkylation of rac-1,3-diphenyl-2-propenyl acetate catalyzed by the palladium-complexes of phosphine–phosphite ligands with 1,1'-binaphthyl- or 1,1'-octahydrobinaphthyl- moiety is reported. The roles of (i) the tether length in directly analogous phosphine–phosphite ligands, (ii) the stereogenic elements in the backbone of PC3OP type of ligands, and (iii) the BINOL moiety in the activities and enantioselectivities of the catalysts are studied. The applicability of these ligands was also evaluated in ethylene and propylene carbonates as green solvents obtaining up to 69% ees with good activity. By using directly analogous phosphine–phosphite ligands the catalytic activity increases steadily with the length of the backbone and with the basicity of the phosphine moiety.

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Keywords
Phosphine–phosphite; Palladium; Allylic alkylation; Enantioselective
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Phosphine–phosphite ligands in the palladium-catalyzed asymmetric allylic alkylation: Electronic and steric effects
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 36, 5 June 2013, Pages 94–97
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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