Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides
Type
ArticleKAUST Grant Number
KUS-11-006-02Date
2010-10Permanent link to this record
http://hdl.handle.net/10754/599445
Metadata
Show full item recordAbstract
Herein an efficient and direct copper-catalyzed coupling of oxazoline-containing aryl bromides with electron-deficient secondary phosphine oxides is reported. The resulting tertiary phosphine oxides can be reduced to prepare a range of PHOX ligands. The presented strategy is a useful alternative to known methods for constructing PHOX derivatives.Citation
McDougal NT, Streuff J, Mukherjee H, Virgil SC, Stoltz BM (2010) Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides. Tetrahedron Letters 51: 5550–5554. Available: http://dx.doi.org/10.1016/j.tetlet.2010.08.039.Sponsors
This publication is based on the work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), the German Academic Exchange Service (DAAD, postdoctoral fellowship to J.S.), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support.Publisher
Elsevier BVJournal
Tetrahedron LettersPubMed ID
21076623PubMed Central ID
PMC2976555ae974a485f413a2113503eed53cd6c53
10.1016/j.tetlet.2010.08.039
Scopus Count
Collections
Publications Acknowledging KAUST SupportRelated articles
- P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides.
- Authors: Dai Q, Li W, Li Z, Zhang J
- Issue date: 2019 Dec 26
- Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction.
- Authors: Zhong CH, Huang W
- Issue date: 2020 Jul 7
- Phosphine Oxides as Stabilizing Ligands for the Palladium-Catalyzed Cross-Coupling of Potassium Aryldimethylsilanolates.
- Authors: Denmark SE, Smith RC, Tymonko SA
- Issue date: 2007 Jun 25
- Computational Analysis on the Pd-Catalyzed C-N Coupling of Ammonia with Aryl Bromides Using a Chelate Phosphine Ligand.
- Authors: Gómez-Orellana P, Lledós A, Ujaque G
- Issue date: 2021 Mar 5
- Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands.
- Authors: Hu Z, Wei XJ, Handelmann J, Seitz AK, Rodstein I, Gessner VH, Gooßen LJ
- Issue date: 2021 Mar 15