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Literature DB >> 23765789

Deprotonation of a borohydride: synthesis of a carbene-stabilized boryl anion.

David A Ruiz¹, Gaël Ung, Mohand Melaimi, Guy Bertrand.

Abstract

An acidic hydride! Thanks to the presence of a π-acceptor cyclic alkyl amino carbene and of two electron-withdrawing nitrile groups, a borohydride reacts with a base to give a carbene-stabilized boryl anion, which reacts with carbon and metal electrophiles at the boron center. Dipp = 2,6-diisopropylphenyl, KHMDS = potassium bis(trimethylsilyl)amide.

Entities: Chemical Disease Gene

Keywords: anions; boron; gold; nucleophiles

Mesh：

Substances：

Year: 2013 PMID： 23765789 PMCID： PMC3712875 DOI： 10.1002/anie.201303457

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

29 in total

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Journal: Angew Chem Int Ed Engl Date: 2006-05-19 Impact factor: 15.336

2. "Umpolung" at boron by reduction of [B(CN)4]- and formation of the dianion [B(CN)3]2-.

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3. A linear, anionic dimetalloborylene complex.

Authors: Holger Braunschweig; Michael Burzler; Rian D Dewhurst; Krzysztof Radacki
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Transition-metal complexes featuring Z-type ligands: agreement or discrepancy between geometry and d(n) configuration?

Authors: Marie Sircoglou; Sébastien Bontemps; Maxime Mercy; Nathalie Saffon; Masashi Takahashi; Ghenwa Bouhadir; Laurent Maron; Didier Bourissou
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Borylcyanocuprate in a one-pot carboboration by a sequential reaction with an electron-deficient alkyne and an organic carbon electrophile.

Authors: Yuri Okuno; Makoto Yamashita; Kyoko Nozaki
Journal: Angew Chem Int Ed Engl Date: 2010-12-22 Impact factor: 15.336

6. Trivalent boron nucleophile as a new tool in organic synthesis: reactivity and asymmetric induction.

Authors: Jessica Cid; Henrik Gulyás; Jorge J Carbó; Elena Fernández
Journal: Chem Soc Rev Date: 2012-02-15 Impact factor: 54.564

7. Group-4 transition-metal boryl complexes: syntheses, structures, boron-metal bonding properties, and application as a polymerization catalyst.

Authors: Tomomi Terabayashi; Takashi Kajiwara; Makoto Yamashita; Kyoko Nozaki
Journal: J Am Chem Soc Date: 2009-10-14 Impact factor: 15.419

8. Boryl anion attacks transition-metal chlorides to form boryl complexes: syntheses, spectroscopic, and structural studies on group 11 borylmetal complexes.

Authors: Yasutomo Segawa; Makoto Yamashita; Kyoko Nozaki
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

9. 31P NMR chemical shifts of carbene-phosphinidene adducts as an indicator of the π-accepting properties of carbenes.

Authors: Olivier Back; Martin Henry-Ellinger; Caleb D Martin; David Martin; Guy Bertrand
Journal: Angew Chem Int Ed Engl Date: 2013-01-31 Impact factor: 15.336

10. Facile splitting of hydrogen and ammonia by nucleophilic activation at a single carbon center.

Authors: Guido D Frey; Vincent Lavallo; Bruno Donnadieu; Wolfgang W Schoeller; Guy Bertrand
Journal: Science Date: 2007-04-20 Impact factor: 47.728

14 in total

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Journal: Eur J Inorg Chem Date: 2017-05-11 Impact factor: 2.524

Review 2. Recent Advances in the Domain of Cyclic (Alkyl)(Amino) Carbenes.

Authors: Saroj Kumar Kushvaha; Ankush Mishra; Herbert W Roesky; Kartik Chandra Mondal
Journal: Chem Asian J Date: 2022-02-26

3. Generation of 1,2-azaboretidines via reduction of ADC borane adducts.

Authors: H Braunschweig; A Gackstatter; T Kupfer; T Scheller; F Hupp; A Damme; N Arnold; W C Ewing
Journal: Chem Sci Date: 2015-04-16 Impact factor: 9.825

4. An overview of N-heterocyclic carbenes.

Authors: Matthew N Hopkinson; Christian Richter; Michael Schedler; Frank Glorius
Journal: Nature Date: 2014-06-26 Impact factor: 49.962

5. Diverse reactivity of a tricoordinate organoboron L₂PhB: (L = oxazol-2-ylidene) towards alkali metal, group 9 metal, and coinage metal precursors.

Authors: Lingbing Kong; Rakesh Ganguly; Yongxin Li; Rei Kinjo
Journal: Chem Sci Date: 2015-02-23 Impact factor: 9.825

6. Nucleophilic addition and substitution at coordinatively saturated boron by facile 1,2-hydrogen shuttling onto a carbene donor.

Authors: Dominic Auerhammer; Merle Arrowsmith; Holger Braunschweig; Rian D Dewhurst; J Oscar C Jiménez-Halla; Thomas Kupfer
Journal: Chem Sci Date: 2017-08-04 Impact factor: 9.825

10. Borylation of fluorinated arenes using the boron-centred nucleophile B(CN)₃^2- - a unique entry to aryltricyanoborates.

Authors: Johannes Landmann; Philipp T Hennig; Nikolai V Ignat'ev; Maik Finze
Journal: Chem Sci Date: 2017-06-26 Impact factor: 9.825