Borylation directed borylation of <i>N</i>-alkyl anilines using iodine activated pyrazaboles

Millet, C. R. P.; Noone, E.; Schellbach, A. V.; Pahl, J.; Łosiewicz, J.; Nichol, G. S.; Ingleson, M. J.

doi:10.1039/d3sc04269c

Cited by 2 publications

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“…In 2023, the Mascareñas group realized iridium-catalyzed C-2 borylation of N -phenylbenzamide in 85% yield, but the noble transition metal and a complex ligand are required (Scheme a) . Metal-free C–H borylation is considered as a powerful tool for building C–B bonds . In 2020, the Shi group reported a boron-mediated acyl-directed o -C–H hydroxylation of indoles and anilines using BBr 3 under metal-free conditions in one pot .…”

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Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr₃

Chen,

Xia,

Huang

et al. 2024

Org. Lett.

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A novel metal-free chemoselective C−H hydroxylation and borylation of N-phenylbenzamides using BBr 3 is described. The protocol generates the corresponding phenols and arylboronic esters in moderate to excellent yields under mild conditions with brilliant chemoselectivity. Additionally, this strategy can be realized in one pot, and several potential bioactive derivatives can be synthesized efficiently. Density functional theory calculations certify that the preferred pathway for this metal-free C−H hydroxylation process is the formation of a five-membered boracycle.2-Hydroxy-N-phenylbenzamides were proven to have a wide range of biological activities, such as antimalarial, antiviral, cryptosporidiosis treatment, and so on (Figure 1). 1 The Letter pubs.acs.org/OrgLett

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confidence: 99%

Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr₃

Chen,

Xia,

Huang

et al. 2024

Org. Lett.

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Unsaturated (C(sp2/sp)–B) Boronic Acid Derivatives

Schneider,

Konowalchuk,

Hall

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Borylation directed borylation of N-alkyl anilines using iodine activated pyrazaboles

Abstract: Doubly electrophilic pyrazabole derivatives (pyrazabole = [H2B(-C3N2H3)]2) combined with one equiv. of base effect the ortho-borylation of N-alkyl anilines. Initial studies found that the bis(trifluoromethane)sulfonimide ([NTf2]-) pyrazabole derivative, [H(NTf2)B(-C3N2H3)]2, is...

Cited by 2 publications

References 48 publications

Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr₃

Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr₃

Unsaturated (C(sp2/sp)–B) Boronic Acid Derivatives

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Borylation directed borylation of N-alkyl anilines using iodine activated pyrazaboles

Abstract: Doubly electrophilic pyrazabole derivatives (pyrazabole = [H2B(-C3N2H3)]2) combined with one equiv. of base effect the ortho-borylation of N-alkyl anilines. Initial studies found that the bis(trifluoromethane)sulfonimide ([NTf2]-) pyrazabole derivative, [H(NTf2)B(-C3N2H3)]2, is...

Cited by 2 publications

References 48 publications

Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr3

Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr3

Unsaturated (C(sp2/sp)–B) Boronic Acid Derivatives

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Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr₃

Chemoselective C–H Hydroxylation and Borylation of N-Phenylbenzamides using BBr₃