P/O Ligand Systems: Facile Synthesis, Structure, and Catalytic Tests of 2′‐Phosphanyl‐1,1′ ‐phenyl‐2‐ols and 2′‐Phosphanyl‐1,1′‐binaphthyl‐2‐ols

Publisher Website
Google Scholar
Abstract
A facile synthesis of 2′‐phosphanyl‐1,1′‐biphenyl‐ and 2′‐phosphanyl‐1,1′ ‐binaphthyl‐2‐ols and their silyl ethers has been developed, consisting of electron‐transfer‐catalyzed ring‐opening of dibenzofuran and dinaphthofuran, respectively, subsequent reaction with chlorophosphanes, and work‐up with acetic acid or ClSiMe3. Studies of the molecular and crystal structures reveals the presence of P—H—O bridging bonds in the more basic tBuPhP derivative and a nearly perpendicular arrangement of the aryl planes in the biphenyl derivatives. The barrier to rotation of the aryl planes about the C–C axis was determined by NMR in the case of the P‐asymmetric derivative 3d, using the appearence of diastereoisomers by atropisomerism and P‐asymmetry. Comparative screening tests of the title compounds, phosphanyl phenols and phosphanylnaphthols in homogeneous Rh‐catalyzed reactions demonstrate catalytic activity in hydroformylation reactions and superior properties of the biphenyl‐ and binaphthyl‐2‐ol derivatives in relation to other P–O ligands.

This publication has 27 references indexed in Scilit: