Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2012 Jul 11;112(7):4246-82.
doi: 10.1021/cr200133c. Epub 2012 Apr 20.

Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective

Timothy S De Vries  1 , Aleksandrs Prokofjevs, Edwin Vedejs
Affiliations
Free PMC article

Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective

Timothy S De Vries et al. Chem Rev. .
Free PMC article
No abstract available

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Boron cation nomenclature and structural representations in current use.
Fig. 2
Fig. 2
Borenium equivalents
Fig. 3
Fig. 3
B3LYP/6-31G* energies for cationic structures from 264 to 72b
Scheme 1
Scheme 1
Electrophilic activation of 1,3-diazaborolidines by protonation or by Lewis acid catalysts
Scheme 2
Scheme 2
Generation of borenium ions by halide abstraction–
Scheme 3
Scheme 3
Borenium ion generation by hydride abstraction–
Scheme 4
Scheme 4
Generation of borenium ion equivalents by hydride abstraction–
Scheme 5
Scheme 5
Minimally stabilized borenium ions by nucleophilic addition-heterolysis,
Scheme 6
Scheme 6
Stereogenic boron structures containing potential leaving groups,
Scheme 7
Scheme 7
Asymmetric memory at stereogenic boron
Scheme 8
Scheme 8
Epimerization at boron and asymmetric transformation
Scheme 9
Scheme 9
Epimerization in chiral salicylaldimine complexes
Scheme 10
Scheme 10
Configurational stability, conformational stability, and stereogenic boron,
Scheme 11
Scheme 11
Oxazaborolidine catalysis in ketone reduction,
Scheme 12
Scheme 12
Chiral oxazaborolidines as sources of borenium salts,,,
Scheme 13
Scheme 13
Enantioselective Diels-Alder reactions catalyzed by oxazaborolidines,,
Scheme 14
Scheme 14
Generation of borenium salt 201 and polymerization catalysis
Scheme 15
Scheme 15
Synthetic applications involving alkoxyborenium intermediates
Scheme 16
Scheme 16
π-Conjugated borenium analogues–
Scheme 17
Scheme 17
π-Conjugated borenium analogues as anion sensors–
Scheme 18
Scheme 18
Intramolecular nitrogen-directed aromatic borylation
Scheme 19
Scheme 19
Intermolecular aromatic borylation using catechol-derived borenium salts
Scheme 20
Scheme 20
Electrophilic borylation of electron-rich aromatic and heteroaromatic substrates
Scheme 21
Scheme 21
Intermolecular borylation using 9-BBN-derived borenium equivalents
Scheme 22
Scheme 22
Activation of triethylamine borane for intermolecular borylation
Scheme 23
Scheme 23
Intramolecular borylation using BBr3/Et2NiPr
Scheme 24
Scheme 24
Intermolecular borylation using BCl3/AlCl3 and 2,6-lutidine or Me2NTol
Scheme 25
Scheme 25
NHC-stabilized borenium salts–
Scheme 26
Scheme 26
NHC borane-amine cyclization
Scheme 27
Scheme 27
Aliphatic C-H insertion
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Shitov OP, Ioffe SL, Tartakovskii VA, Novikov SS. Russ Chem Rev. 1970;39:905.
    1. Kölle P, Nöth H. Chem Rev. 1985;85:399.
    1. Piers WE, Bourke SC, Conroy KD. Angew Chem Int Ed. 2005;44:5016. - PubMed
    1. Wiberg E, Schuster K. Z Anorg Allg Chem. 1933;213:77.
    2. Wiberg E, Schuster K. Z Anorg Allg Chem. 1933;213:89.
    1. Wiberg E, Hertwig K. Z Anorg Chem. 1947;255:141.

Publication types