Citation: Zhenyu Yao, Xing Lin, Remi Chauvin, Lianhui Wang, Emmanuel Gras, Xiuling Cui. Phosphine-phosphonium ylides as ligands in palladium-catalysed C₂-H arylation of benzoxazoles[J]. Chinese Chemical Letters, ;2020, 31(12): 3250-3254. doi: 10.1016/j.cclet.2020.04.008 shu

Phosphine-phosphonium ylides as ligands in palladium-catalysed C₂-H arylation of benzoxazoles

Zhenyu Yao ^a ,
Xing Lin ^a ,
Remi Chauvin ^{a, b, **,} ,
Lianhui Wang ^a ,
Emmanuel Gras ^b ,
Xiuling Cui ^{a, *,}

a.
Engineering Research Centre of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China
b.
Laboratory of Coordination Chemistry (LCC), CNRS & Universite' de Toulouse (UPS, INP), Toulouse 31077 Cedex 4, France

^**

chauvin@lcc-toulouse.fr

cuixl@hqu.edu.cn

Received Date: 5 March 2020
Revised Date: 29 March 2020
Accepted Date: 6 April 2020
Available Online: 18 April 2020

Figures(3)

As balanced electron-rich P, C-chelating ligands, phosphine-phosphonium-ylides are considered for their ability to in situ promote palladium-catalysed direct C(sp²)-H arylation. Using methyl phosphonium salts of 2, 2'-bis(diphenylphosphino)-1, 1'-binaphtyl ("methyl-BINAPIUM") as ylide precursors under optimized reaction conditions, arylation of benzoxazole was found to proceed in moderate to high yield to give functional 2-aryl benzoxazoles. A strong anion effect of the non-salt free ylide was evidenced (TfO^- > I^- > PF₆^- ≈ salt-free). This first example of phosphonium ylides as ligands in catalytic C-H activation extends the prospect of their general implementation in homogeneous transition metal catalysis.
- Electron-rich,
- Ligands,
- Phosphine-phosphonium-ylides,
- Benzixazole,
- C-H activation
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Phosphine-phosphonium ylides as ligands in palladium-catalysed C2-H arylation of benzoxazoles

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Phosphine-phosphonium ylides as ligands in palladium-catalysed C₂-H arylation of benzoxazoles