Journal Articles Chinese Chemical Letters Year : 2020

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

Abstract

As balanced electron-rich P,C-chelating ligands, phosphine-phosphonium-ylides are considered for their ability to in situ promote palladium-catalysed direct sp2-CH 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.

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hal-02613316 , version 1 (02-01-2023)

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Zhenyu Yao, Xing Lin, Rémi Chauvin, Lianhui Wang, Emmanuel Gras, et al.. Phosphine-phosphonium ylides as ligands in palladium-catalysed C2-H arylation of benzoxazoles. Chinese Chemical Letters, 2020, 31 (12), pp.3250-3254. ⟨10.1016/j.cclet.2020.04.008⟩. ⟨hal-02613316⟩
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