Chemoselective boron-carbon bond cleavage by hydroboration of borirenes

Holger Braunschweig; Thomas Herbst; Krzysztof Radacki; Gernot Frenking; Mehmet Ali Celik

doi:10.1002/chem.200901749

Chemoselective boron-carbon bond cleavage by hydroboration of borirenes

Holger Braunschweig, Thomas Herbst, Krzysztof Radacki, Gernot Frenking, Mehmet Ali Celik

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

17 Scopus citations

Abstract

We report on the hydroboration of 1-[bis(trimethylsilyl)amino]-2,3- diethylborirene (3) with 9-borabicyclo-[3.3.1]nonane (9-BBN), which led through ring-opening to an amino-(vinyl)borane. The viscous borane was subsequently converted into a crystalline borate on treatment with MeLi.Both compounds were fully characterized by multinuclear NMR spectroscopy and in case of the latter by singlecrystal X-ray diffraction analysis. To elucidate the reaction mechanism of the unexpected boron-carbon bond cleavage, DFT calculations of energy minima and transition states for the hydroboration were carried out.

Original language	English
Pages (from-to)	12099-12106
Number of pages	8
Journal	Chemistry - A European Journal
Volume	15
Issue number	44
DOIs	https://doi.org/10.1002/chem.200901749
State	Published - 2009
Externally published	Yes

Keywords

Aromaticity
Boracyclopolyenes
Borirenes
Boron
Hydroboration

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title = "Chemoselective boron-carbon bond cleavage by hydroboration of borirenes",

abstract = "We report on the hydroboration of 1-[bis(trimethylsilyl)amino]-2,3- diethylborirene (3) with 9-borabicyclo-[3.3.1]nonane (9-BBN), which led through ring-opening to an amino-(vinyl)borane. The viscous borane was subsequently converted into a crystalline borate on treatment with MeLi.Both compounds were fully characterized by multinuclear NMR spectroscopy and in case of the latter by singlecrystal X-ray diffraction analysis. To elucidate the reaction mechanism of the unexpected boron-carbon bond cleavage, DFT calculations of energy minima and transition states for the hydroboration were carried out.",

keywords = "Aromaticity, Boracyclopolyenes, Borirenes, Boron, Hydroboration",

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T1 - Chemoselective boron-carbon bond cleavage by hydroboration of borirenes

AU - Braunschweig, Holger

AU - Herbst, Thomas

AU - Radacki, Krzysztof

AU - Frenking, Gernot

AU - Ali Celik, Mehmet

PY - 2009

Y1 - 2009

N2 - We report on the hydroboration of 1-[bis(trimethylsilyl)amino]-2,3- diethylborirene (3) with 9-borabicyclo-[3.3.1]nonane (9-BBN), which led through ring-opening to an amino-(vinyl)borane. The viscous borane was subsequently converted into a crystalline borate on treatment with MeLi.Both compounds were fully characterized by multinuclear NMR spectroscopy and in case of the latter by singlecrystal X-ray diffraction analysis. To elucidate the reaction mechanism of the unexpected boron-carbon bond cleavage, DFT calculations of energy minima and transition states for the hydroboration were carried out.

AB - We report on the hydroboration of 1-[bis(trimethylsilyl)amino]-2,3- diethylborirene (3) with 9-borabicyclo-[3.3.1]nonane (9-BBN), which led through ring-opening to an amino-(vinyl)borane. The viscous borane was subsequently converted into a crystalline borate on treatment with MeLi.Both compounds were fully characterized by multinuclear NMR spectroscopy and in case of the latter by singlecrystal X-ray diffraction analysis. To elucidate the reaction mechanism of the unexpected boron-carbon bond cleavage, DFT calculations of energy minima and transition states for the hydroboration were carried out.

KW - Aromaticity

KW - Boracyclopolyenes

KW - Borirenes

KW - Boron

KW - Hydroboration

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DO - 10.1002/chem.200901749

M3 - 文章

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SN - 0947-6539

VL - 15

SP - 12099

EP - 12106

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 44

ER -

Chemoselective boron-carbon bond cleavage by hydroboration of borirenes

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Keywords

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