A boronium ion with exceptional electrophilicity

Aleksandrs Prokofjevs; Jeff W. Kampf; Edwin Vedejs

doi:10.1002/anie.201005663

A boronium ion with exceptional electrophilicity

Aleksandrs Prokofjevs
, Jeff W. Kampf
, Edwin Vedejs

Chemistry

University of Michigan, Ann Arbor

Research output: Contribution to journal › Article › peer-review

109 Scopus citations

Abstract

Barely bidentate: The adduct of dimethylamino naphthalene (proton sponge) and 9-BBN-NTf2 is activated by steric hinderance for intermolecular borylation (see scheme). A contrasting addition/elimination pathway is favored when using monodentate triethylamine which gives the first observable borenium salt (9-BBN-NEt3 + Tf2N-) lacking any n- or π-donor substitutents. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	2098-2101
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	9
DOIs	https://doi.org/10.1002/anie.201005663
State	Published - Feb 25 2011

Keywords

aromatic substitution
borenium ions
boron
boronium ions
borylation

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abstract = "Barely bidentate: The adduct of dimethylamino naphthalene (proton sponge) and 9-BBN-NTf2 is activated by steric hinderance for intermolecular borylation (see scheme). A contrasting addition/elimination pathway is favored when using monodentate triethylamine which gives the first observable borenium salt (9-BBN-NEt3 + Tf2N-) lacking any n- or π-donor substitutents. {\textcopyright} 2011 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

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AU - Prokofjevs, Aleksandrs

AU - Kampf, Jeff W.

AU - Vedejs, Edwin

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N2 - Barely bidentate: The adduct of dimethylamino naphthalene (proton sponge) and 9-BBN-NTf2 is activated by steric hinderance for intermolecular borylation (see scheme). A contrasting addition/elimination pathway is favored when using monodentate triethylamine which gives the first observable borenium salt (9-BBN-NEt3 + Tf2N-) lacking any n- or π-donor substitutents. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - Barely bidentate: The adduct of dimethylamino naphthalene (proton sponge) and 9-BBN-NTf2 is activated by steric hinderance for intermolecular borylation (see scheme). A contrasting addition/elimination pathway is favored when using monodentate triethylamine which gives the first observable borenium salt (9-BBN-NEt3 + Tf2N-) lacking any n- or π-donor substitutents. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - aromatic substitution

KW - borenium ions

KW - boron

KW - boronium ions

KW - borylation

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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A boronium ion with exceptional electrophilicity

Abstract

Keywords

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