Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization

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Abstract

Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.
Original languageEnglish
Pages (from-to)16363-16366
Number of pages4
JournalAngewandte Chemie-International Edition
Volume56
Issue number51
Early online date8 Nov 2017
DOIs
Publication statusPublished - 18 Dec 2017

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Magnesium
Anions
single bond
nonane
diborane

Cite this

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title = "Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization",
abstract = "Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.",
author = "Michael Hill and Mary Mahon and Claire McMullin and Anne-Frederique Pecharman",
year = "2017",
month = "12",
day = "18",
doi = "10.1002/anie.201709902",
language = "English",
volume = "56",
pages = "16363--16366",
journal = "Angewandte Chemie-International Edition",
issn = "1433-7851",
publisher = "WILEY-V C H VERLAG GMBH",
number = "51",

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TY - JOUR

T1 - Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization

AU - Hill, Michael

AU - Mahon, Mary

AU - McMullin, Claire

AU - Pecharman, Anne-Frederique

PY - 2017/12/18

Y1 - 2017/12/18

N2 - Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.

AB - Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.

U2 - 10.1002/anie.201709902

DO - 10.1002/anie.201709902

M3 - Article

VL - 56

SP - 16363

EP - 16366

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

IS - 51

ER -