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o-Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications
- o-Hydroxyarylphosphanes are fascinating compounds by their multiple-reactivity features, attributed to the ambident hard and soft Lewis- and also Brønstedt acid-base properties, wide tuning opportunities via backbone substituents with ±mesomeric and inductive, at P and in o-position to P and O also steric effects, and in addition, the configurational stability at three-valent phosphorus. Air sensitivity may be overcome by reversible protection with BH3, but the easy oxidation to P(V)-compounds may also be used. Since the first reports on the title compounds ca. 50 years ago the multiple reactivity has led to versatile applications. This includes various P−E−O and P=C−O heterocycles, a multitude of O-substituted derivatives including acyl derivatives for traceless Staudinger couplings of biomolecules with labels or functional substituents, phosphane-phosphite ligands, which like the o-phosphanylphenols itself form a range of transition metal complexes and catalysts. Also main group metal complexes and (bi)arylphosphonium-organocatalysts are derived. Within this review the various strategies for the access of the starting materials are illuminated, including few hints to selected applications.
Author: | Joachim W. Heinicke |
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URN: | urn:nbn:de:gbv:9-opus-109371 |
DOI: | https://doi.org/10.1002/chem.202302740 |
ISSN: | 1521-3765 |
Parent Title (English): | Chemistry - A European Journal |
Publisher: | Wiley |
Place of publication: | Hoboken, NJ |
Document Type: | Article |
Language: | English |
Date of Publication (online): | 2023/10/31 |
Date of first Publication: | 2024/01/26 |
Release Date: | 2024/03/27 |
Tag: | P,O heterocycles; P,O ligands; catalyses; phosphanes; synthetic methods |
Volume: | 30 |
Issue: | 6 |
Article Number: | e202302740 |
Page Number: | 31 |
Faculties: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie |
Collections: | weitere DFG-förderfähige Artikel |
Licence (German): | Creative Commons - Namensnennung-Nicht kommerziell-Keine Bearbeitung 4.0 International |