Synthesis of Unsymmetrical Diboranes by Diborane Metathesis

Anne-Frederique Pecharman; Michael Hill; Mary Mahon

doi:10.1002/anie.201803607

Synthesis of Unsymmetrical Diboranes by Diborane Metathesis

Anne-Frederique Pecharman, Michael Hill, Mary Mahon

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Abstract

Reactions of readily accessible magnesium-centered pinacolatoboryl nucleophiles with [(Ph ₂B) ₂O] result in B−O bond activation of the diphenylborinic anhydride. Although [pinBBPh ₂] is apparently generated when the nucleophilic boron unit is derived in situ from a magnesium diboranate, it cannot be isolated owing to its onward derivatization by a further {Bpin} ⁻ equivalent. A reaction with a terminal magnesium boryl species similarly provides a boryloxide byproduct. In this case, however, the unsymmetrical B(sp ²)−B(sp ³) diborane may be intercepted as its DMAP adduct.

Original language	English
Pages (from-to)	10688-10691
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	57
Issue number	33
Early online date	6 Jun 2018
DOIs	https://doi.org/10.1002/anie.201803607
Publication status	Published - 6 Aug 2018

Keywords

boranes
boron
diboranes
magnesium
main group chemistry

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201803607

Diborane Synthesis by Diboron Metathesis_TEMPLATE_Accepted Article.pdf
This is the peer reviewed version of the following article: Hill, M. ., Pécharman, A. and Mahon, M. (2018), Unsymmetrical Diborane Synthesis by Diborane Metathesis. Angew. Chem. Int. Ed., which has been published in final form at https://doi.org/10.1002/anie.201803607. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Accepted author manuscript, 953 KBLicence: Unspecified

Cite this

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title = "Synthesis of Unsymmetrical Diboranes by Diborane Metathesis",

abstract = "Reactions of readily accessible magnesium-centered pinacolatoboryl nucleophiles with [(Ph 2B) 2O] result in B−O bond activation of the diphenylborinic anhydride. Although [pinBBPh 2] is apparently generated when the nucleophilic boron unit is derived in situ from a magnesium diboranate, it cannot be isolated owing to its onward derivatization by a further {Bpin} − equivalent. A reaction with a terminal magnesium boryl species similarly provides a boryloxide byproduct. In this case, however, the unsymmetrical B(sp 2)−B(sp 3) diborane may be intercepted as its DMAP adduct. ",

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author = "Anne-Frederique Pecharman and Michael Hill and Mary Mahon",

year = "2018",

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T1 - Synthesis of Unsymmetrical Diboranes by Diborane Metathesis

AU - Pecharman, Anne-Frederique

AU - Hill, Michael

AU - Mahon, Mary

PY - 2018/8/6

Y1 - 2018/8/6

N2 - Reactions of readily accessible magnesium-centered pinacolatoboryl nucleophiles with [(Ph 2B) 2O] result in B−O bond activation of the diphenylborinic anhydride. Although [pinBBPh 2] is apparently generated when the nucleophilic boron unit is derived in situ from a magnesium diboranate, it cannot be isolated owing to its onward derivatization by a further {Bpin} − equivalent. A reaction with a terminal magnesium boryl species similarly provides a boryloxide byproduct. In this case, however, the unsymmetrical B(sp 2)−B(sp 3) diborane may be intercepted as its DMAP adduct.

AB - Reactions of readily accessible magnesium-centered pinacolatoboryl nucleophiles with [(Ph 2B) 2O] result in B−O bond activation of the diphenylborinic anhydride. Although [pinBBPh 2] is apparently generated when the nucleophilic boron unit is derived in situ from a magnesium diboranate, it cannot be isolated owing to its onward derivatization by a further {Bpin} − equivalent. A reaction with a terminal magnesium boryl species similarly provides a boryloxide byproduct. In this case, however, the unsymmetrical B(sp 2)−B(sp 3) diborane may be intercepted as its DMAP adduct.

KW - boranes

KW - boron

KW - diboranes

KW - magnesium

KW - main group chemistry

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DO - 10.1002/anie.201803607

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JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

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ER -

Synthesis of Unsymmetrical Diboranes by Diborane Metathesis

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Michael Hill

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Synthesis of Unsymmetrical Diboranes by Diborane Metathesis

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Michael Hill

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