Chemistry:2-Diphenylphosphinobenzaldehyde
From HandWiki
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| Preferred IUPAC name
2-(Diphenylphosphanyl)benzaldehyde | |
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3D model (JSmol)
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| Properties | |
| C19H15OP | |
| Appearance | yellow solid |
| Melting point | 118 to 119 °C (244 to 246 °F; 391 to 392 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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2-Diphenylphosphinobenzaldehyde is a phosphine ligand with the formula (C6H5)2PC6H4CHO. It is a yellow solid that dissolves in common organic solvents.
Synthesis and reactions
2-Diphenylphosphinobenzaldehyde was first prepared by the reaction of chlorodiphenylphosphine with the Grignard reagent derived from the protected 2-bromobenzaldehyde, followed by deprotection.[1][2] It can also be derived from (2-lithiophenyl)diphenylphosphine.
The compound condenses with a variety of amines to give phosphine-imine and phosphine-amine ligands.[3] [4]
References
- ↑ Hoots, John E.; Rauchfuss, Thomas B.; Wrobleski, Debra A.; Knachel, Howard C. (2007). "39. Substituted Triaryl Phosphines". Inorganic Syntheses. pp. 175–179. doi:10.1002/9780470132524.ch39. ISBN 9780470132524.
- ↑ Schiemenz, Guenter P.; Kaack, Hermann "Aromatische Phosphine mit Substituenten zweiter Ordnung, XIII. Triarylphosphine mit mehreren Carbonyl-Funktionen durch Grignard-Synthese (Aromatic phosphines with second order substituents. XIII. Preparation of triarylphosphines with several carbonyl functions by Grignard synthesis)" Justus Liebigs Annalen der Chemie 1973, vol. 9, pp. 1480-93. doi:10.1002/jlac.197319730910.
- ↑ Degrado, Sylvia J.; Mizutani, Hirotake; Hoveyda, Amir H. (2001). "Modular Peptide-Based Phosphine Ligands in Asymmetric Catalysis: Efficient and Enantioselective Cu-Catalyzed Conjugate Additions to Five-, Six-, and Seven-Membered Cyclic Enones". Journal of the American Chemical Society 123 (4): 755–756. doi:10.1021/ja003698p. PMID 11456598.
- ↑ Hu, Anjing; Zhang, Zhan-Ming; Xiao, Yuanjing; Zhang, Junliang (2020). "Stereoselective Synthesis of Chiral Sulfinamide Monophosphine Ligands (Ming-Phos)(S, Rs)-M". Organic Syntheses 97: 262–273. doi:10.15227/orgsyn.097.0262.
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