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Literature DB >> 26095444

1,2-Azaborine: The Boron-Nitrogen Derivative of ortho-Benzyne.

Klara Edel¹, Sarah A Brough¹, Ashley N Lamm², Shih-Yuan Liu^2,3, Holger F Bettinger⁴.

Abstract

The BN analogue of ortho-benzyne, 1,2-azaborine, is generated by flash vacuum pyrolysis, trapped under cryogenic conditions, and studied by direct spectroscopic techniques. The parent BN aryne spontaneously binds N2 and CO2, thus demonstrating its highly reactive nature. The interaction with N2 is photochemically reversible. The CO2 adduct of 1,2-azaborine is a cyclic carbamate which undergoes photocleavage, thus resulting in overall CO2 splitting.

Entities: Chemical Species

Keywords: ab initio calculations; arynes; boron; matrix isolation; nitrogen heterocycles

Mesh：

Substances：

Year: 2015 PMID： 26095444 PMCID： PMC4564995 DOI： 10.1002/anie.201502967

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

26 in total

Review 1. A comprehensive history of arynes in natural product total synthesis.

Authors: Pamela M Tadross; Brian M Stoltz
Journal: Chem Rev Date: 2012-03-23 Impact factor: 60.622

2. Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes.

Authors: Anup Bhunia; Santhivardhana Reddy Yetra; Akkattu T Biju
Journal: Chem Soc Rev Date: 2012-01-26 Impact factor: 54.564

3. Arynes and cyclohexyne in natural product synthesis.

Authors: Christian M Gampe; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2012-03-15 Impact factor: 15.336

4. Azaboradibenzo[6]helicene: carrier inversion induced by helical homochirality.

Authors: Takuji Hatakeyama; Sigma Hashimoto; Tsuyoshi Oba; Masaharu Nakamura
Journal: J Am Chem Soc Date: 2012-11-27 Impact factor: 15.419

5. BN-phenanthryne: cyclotetramerization of an 1,2-azaborine derivative.

Authors: Matthias Müller; Cäcilia Maichle-Mössmer; Holger F Bettinger
Journal: Angew Chem Int Ed Engl Date: 2014-07-15 Impact factor: 15.336

6. Frustrated Lewis pairs: from concept to catalysis.

Authors: Douglas W Stephan
Journal: Acc Chem Res Date: 2014-12-23 Impact factor: 22.384

7. Antiaromaticity to aromaticity: from boroles to 1,2-azaborinines by ring expansion with azides.

Authors: Holger Braunschweig; Christian Hörl; Lisa Mailänder; Krzysztof Radacki; Johannes Wahler
Journal: Chemistry Date: 2014-06-25 Impact factor: 5.236

8. BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues.

Authors: Daniel H Knack; Jonathan L Marshall; Gregory P Harlow; Agnieszka Dudzik; Maciej Szaleniec; Shih-Yuan Liu; Johann Heider
Journal: Angew Chem Int Ed Engl Date: 2013-01-28 Impact factor: 15.336

6. Solution Phase Reactivity of Dibenzo[c,e][1,2]azaborinine: Activation and Insertion into Si-E Single Bonds (E=H, OSi(CH₃ )₃ , F, Cl) by a BN-Aryne.

Authors: Constanze Keck; Jennifer Hahn; Divanshu Gupta; Holger F Bettinger
Journal: Chemistry Date: 2021-12-02 Impact factor: 5.020

6 in total

1,2-Azaborine: The Boron-Nitrogen Derivative of ortho-Benzyne.

Review 1. A comprehensive history of arynes in natural product total synthesis.

2. Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes.

3. Arynes and cyclohexyne in natural product synthesis.

4. Azaboradibenzo[6]helicene: carrier inversion induced by helical homochirality.

5. BN-phenanthryne: cyclotetramerization of an 1,2-azaborine derivative.

6. Frustrated Lewis pairs: from concept to catalysis.

7. Antiaromaticity to aromaticity: from boroles to 1,2-azaborinines by ring expansion with azides.

8. BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues.

9. Theoretical studies of borazynes and azaborines.

10. Intramolecular frustrated lewis pairs: formation and chemical features.

Review 1. The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications.

2. Superelectrophilicity of 1,2-Azaborine: Formation of Xenon and Carbon Monoxide Adducts.

3. The Dewar Isomer of 1,2-Dihydro-1,2-azaborinines: Isolation, Fragmentation, and Energy Storage.

4. Reactivity of a coordinated inorganic acetylene unit, HBNH, and the azidoborane cation [HB(N₃)]^.

5. Ge=B π-Bonding: Synthesis and Reversible [2+2] Cycloaddition of Germaborenes.

6. Solution Phase Reactivity of Dibenzo[c,e][1,2]azaborinine: Activation and Insertion into Si-E Single Bonds (E=H, OSi(CH₃ )₃ , F, Cl) by a BN-Aryne.