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Literature DB >> 22032808

Generation of a carbene-stabilized bora-borylene and its insertion into a C-H bond.

Philipp Bissinger¹, Holger Braunschweig, Alexander Damme, Rian D Dewhurst, Thomas Kupfer, Krzysztof Radacki, Katharina Wagner.

Abstract

A novel NHC adduct of a dihalodiborane(4), 1, is reduced by KC(8) with formation of the five-membered boracycle 2. The reaction most likely proceeds via C-H insertion of an intermediate NHC-stabilized free bora-borylene species.

Entities: Chemical

Year: 2011 PMID： 22032808 DOI： 10.1021/ja208372k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

13 in total

1. Thermal Dehydrogenation of Base-Stabilized B2H5(+) Complexes and Its Role in C-H Borylation.

Authors: Aleksandrs Prokofjevs
Journal: Angew Chem Int Ed Engl Date: 2015-09-17 Impact factor: 15.336

2. Controlled homocatenation of boron on a transition metal.

Authors: Holger Braunschweig; Qing Ye; Alfredo Vargas; Rian D Dewhurst; Krzysztof Radacki; Alexander Damme
Journal: Nat Chem Date: 2012-06-17 Impact factor: 24.427

3. Synthesis and hydrogenation of polycyclic aromatic hydrocarbon-substituted diborenes via uncatalysed hydrogenative B-C bond cleavage.

Authors: Alexander Okorn; Arumugam Jayaraman; Lukas Englert; Merle Arrowsmith; Theresa Swoboda; Jeanette Weigelt; Carina Brunecker; Merlin Hess; Anna Lamprecht; Carsten Lenczyk; Maximilian Rang; Holger Braunschweig
Journal: Chem Sci Date: 2022-06-14 Impact factor: 9.969

4. 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

5. Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors: Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2015-08-11 Impact factor: 15.419

6. B-B vs. B-H Bond Activation in a (μ-Hydrido)diborane(4) Anion upon Cycloaddition with CO₂ , Isocyanates, or Carbodiimides.

Authors: Timo Trageser; Dariusz Bebej; Michael Bolte; Hans-Wolfram Lerner; Matthias Wagner
Journal: Angew Chem Int Ed Engl Date: 2021-05-07 Impact factor: 15.336

Generation of a carbene-stabilized bora-borylene and its insertion into a C-H bond.

1. Thermal Dehydrogenation of Base-Stabilized B2H5(+) Complexes and Its Role in C-H Borylation.

2. Controlled homocatenation of boron on a transition metal.

3. Synthesis and hydrogenation of polycyclic aromatic hydrocarbon-substituted diborenes via uncatalysed hydrogenative B-C bond cleavage.

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

5. Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

6. B-B vs. B-H Bond Activation in a (μ-Hydrido)diborane(4) Anion upon Cycloaddition with CO₂ , Isocyanates, or Carbodiimides.

7. Reactions of Dihaloboranes with Electron-Rich 1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes.

8. Synthesis and reduction chemistry of mixed-Lewis-base-stabilised chloroborylenes.

9. Facile scission of isonitrile carbon-nitrogen triple bond using a diborane(4) reagent.

10. A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.