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Article Dans Une Revue Angewandte Chemie International Edition Année : 2022

Metal‐Free Phosphorus‐Directed Borylation of C(sp2)−H Bonds

Résumé

Spectacular progress has recently been achieved in transition metal-catalyzed C−H borylation of phosphines as well as directed electrophilic C−H borylation. As shown here, P-directed electrophilic borylation provides a new, straightforward, and efficient access to phosphine–boranes. It operates under metal-free conditions and leverages simple, readily available substrates. It is applicable to a broad range of backbones (naphthyl, biphenyl, N-phenylpyrrole, binaphthyl, benzyl, naphthylmethyl) and gives facile access to various substitution patterns at boron (by varying the boron electrophile or post-derivatizing the borane moiety). NMR monitoring supports the involvement of P-stabilized borenium cations as key intermediates. DFT calculations reveal the existence and stabilizing effect of π-arene/boron interactions in the (biphenyl)(i-Pr)2P→BBr2+ species.
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Dates et versions

hal-03509543 , version 1 (09-10-2022)

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Citer

Omar Sadek, Arnaud Le Gac, Nereida Hidalgo, Sonia Mallet‐ladeira, Karinne Miqueu, et al.. Metal‐Free Phosphorus‐Directed Borylation of C(sp2)−H Bonds. Angewandte Chemie International Edition, 2022, 61 (1), pp.e202110102. ⟨10.1002/anie.202110102⟩. ⟨hal-03509543⟩
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