Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides
Abstract
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 LettersISSN
0040-4039PubMed ID
21076623PubMed Central ID
PMC2976555Handle URI
http://hdl.handle.net/10754/599445ae974a485f413a2113503eed53cd6c53
10.1016/j.tetlet.2010.08.039
Scopus Count
Collections
Publications Acknowledging KAUST SupportRelated articles
- 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
- Copper(II)-catalyzed C-O coupling of aryl bromides with aliphatic diols: synthesis of ethers, phenols, and benzo-fused cyclic ethers.
- Authors: Liu Y, Park SK, Xiao Y, Chae J
- Issue date: 2014 Jul 14
- Palladium-catalyzed sonogashira and hiyama reactions using phosphine-free hydrazone ligands.
- Authors: Mino T, Shirae Y, Saito T, Sakamoto M, Fujita T
- Issue date: 2006 Dec 8
- Copper-Catalyzed Radical/Radical C(sp 3)-H/P-H Cross-Coupling: α-Phosphorylation of Aryl Ketone O-Acetyloximes.
- Authors: Ke J, Tang Y, Yi H, Li Y, Cheng Y, Liu C, Lei A
- Issue date: 2015 May 26
- Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides.
- Authors: Fu T, Qiao H, Peng Z, Hu G, Wu X, Gao Y, Zhao Y
- Issue date: 2014 May 14