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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
Author(s) -
Kadyrov Renat,
Heinicke Joachim,
Kindermann Markus K.,
Heller Detlef,
Fischer Christine,
Selke Rüdiger,
Fischer Axel K.,
Jones Peter G.
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971301118
Subject(s) - chemistry , aryl , atropisomer , catalysis , diastereomer , biphenyl , stereochemistry , ligand (biochemistry) , medicinal chemistry , organic chemistry , biochemistry , alkyl , receptor
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 ClSiMe 3 . Studies of the molecular and crystal structures reveals the presence of P—H—O bridging bonds in the more basic t BuPhP 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.