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Fundamental and Applied Properties of Borocations

  • Michael J. Ingleson
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 49)

Abstract

The past 5 years has witnessed considerable growth in the field of borocation chemistry with a multitude of new cations containing 2, 3 and 4 coordinate boron centres reported. Perhaps more significant has been the expansion in the synthetic utility of borocations as stoichiometric reagents and catalysts. It is these new applications of borocations that are the primary focus of this article which concentrates on reports from 2009 to the end of June 2014. The correlation between structure and reactivity in these recent studies will be emphasised to aid in the future design of new borocations for specific targeted outcomes.

Keywords

Borenium Borinium Borocations Boronium Borylation Dehydroboration Electrophiles Haloboration Hydroboration Lewis acid catalysis 

Abbreviations

[NTf2]

Triflimide N(SO2CF3)2

[OTf]

Triflate OSO2CF3

BBN

9-Borabicyclo[3.3.1]nonane

Cat

Catecholato ([o-C6H4O2]2−)

CatS2

Thiocatecholato ([o-C6H4S2]2−)

CIA

Chloride ion affinity

DABCO

Diazabicyclo[2.2.2]octane

DIPP

2,6-Disopropylbenzene

DOSY

Diffusion-ordered NMR spectroscopy

FIA

Fluoride ion affinity

FLP

Frustrated Lewis pair

HIA

Hydride ion affinity

KIE

Kinetic isotope effect

Mes

Mesityl (2,4,6-Me3-C6H2)

NHC

N-Heterocyclic carbene

PCM

Polarisation continuum model

Pin

Pinacolato ([OC(Me)2C(Me)2O]2−)

SEAr

Electrophilic aromatic substitution

X-DMAP

N,N-Dimethylaminopyridine (x = 2 or 4)

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.School of ChemistryThe University of ManchesterManchesterUK

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