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Literature DB >> 23749749

Boron-substituted 1,3-dihydro-1,3-azaborines: synthesis, structure, and evaluation of aromaticity.

Senmiao Xu¹, Tanya C Mikulas, Lev N Zakharov, David A Dixon, Shih-Yuan Liu.

Abstract

Getting the family together: A general synthetic strategy based on nucleophilic substitution provided B-substituted 1,3-dihydro-1,3-azaborines (see scheme), BN isosteres of arenes with potential for application in biomedicine and materials science. Experimental structural analysis and calculations suggest that the aromaticity of the 1,3-dihydro-1,3-azaborine heterocycle is intermediate between that of benzene and that of 1,2-dihydro-1,2-azaborine.

Entities: Chemical Species

Keywords: aromaticity; azaborines; boron; heterocycles; synthetic methods

Mesh：

Substances：

Year: 2013 PMID： 23749749 PMCID： PMC3813462 DOI： 10.1002/anie.201302660

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

22 in total

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Journal: Chem Rev Date: 2005-10 Impact factor: 60.622

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Authors: Mihaela Negru; Dieter Schollmeyer; Horst Kunz
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

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Authors: Adam J V Marwitz; Myrna H Matus; Lev N Zakharov; David A Dixon; Shih-Yuan Liu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Molecular double-bond covalent radii for elements Li-E112.

Authors: Pekka Pyykkö; Michiko Atsumi
Journal: Chemistry Date: 2009-11-23 Impact factor: 5.236

5. 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

6. 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

7. Crystal clear structural evidence for electron delocalization in 1,2-dihydro-1,2-azaborines.

Authors: Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2008-05-14 Impact factor: 15.419

8. Diversity through isosterism: the case of boron-substituted 1,2-dihydro-1,2-azaborines.

Authors: Adam J V Marwitz; Eric R Abbey; Jesse T Jenkins; Lev N Zakharov; Shih-Yuan Liu
Journal: Org Lett Date: 2007-10-18 Impact factor: 6.005

9. Synthesis and reactivity of a bis(dimesitylboryl)azaborine and its fluoride sensing ability.

Authors: Tomohiro Agou; Masaki Sekine; Junji Kobayashi; Takayuki Kawashima
Journal: Chem Commun (Camb) Date: 2009-02-20 Impact factor: 6.222

10. Boron mimetics: 1,2-dihydro-1,2-azaborines bind inside a nonpolar cavity of T4 lysozyme.

Authors: Lijun Liu; Adam J V Marwitz; Brian W Matthews; Shih-Yuan Liu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

11 in total

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

Authors: Zachary X Giustra; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2018-01-17 Impact factor: 15.419

2. Medicinal Chemistry Profiling of Monocyclic 1,2-Azaborines.

Authors: Peng Zhao; David O Nettleton; Rajeshri G Karki; Frédéric J Zécri; Shih-Yuan Liu
Journal: ChemMedChem Date: 2017-02-21 Impact factor: 3.466

3. 1,2-Azaborine's Distinct Electronic Structure Unlocks Two New Regioisomeric Building Blocks via Resolution Chemistry.

Authors: Cameron R McConnell; Fredrik Haeffner; Andrew W Baggett; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2019-05-23 Impact factor: 15.419

4. Thermodynamically Controlled, Dynamic Binding of Diols to a 1,2-BN Cyclohexane Derivative.

Authors: Gregory P Harlow; Lev N Zakharov; Gang Wu; Shih-Yuan Liu
Journal: Organometallics Date: 2013 Impact factor: 3.876

5. 1,3,2,5-Diazadiborinine featuring nucleophilic and electrophilic boron centres.

Authors: Di Wu; Lingbing Kong; Yongxin Li; Rakesh Ganguly; Rei Kinjo
Journal: Nat Commun Date: 2015-06-15 Impact factor: 14.919

6. Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines.

Authors: Geraint H M Davies; Asma Mukhtar; Borna Saeednia; Fatemeh Sherafat; Christopher B Kelly; Gary A Molander
Journal: J Org Chem Date: 2017-05-09 Impact factor: 4.354

7. Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins.

Authors: Katherine Boknevitz; James S Italia; Bo Li; Abhishek Chatterjee; Shih-Yuan Liu
Journal: Chem Sci Date: 2019-04-15 Impact factor: 9.825

8. Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons.

Authors: Hang Xiao; Tao Li; Xiao-Li Sun; Wen-Ming Wan; Hongli Bao; Qingrong Qian; Qinghua Chen
Journal: Molecules Date: 2022-01-05 Impact factor: 4.411

9. Selectivity in the Elaboration of Bicyclic Borazarenes.

Authors: Ayan Bhattacharjee; Geraint H M Davies; Borna Saeednia; Steven R Wisniewski; Gary A Molander
Journal: Adv Synth Catal Date: 2020-12-23 Impact factor: 5.837

10. Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components.

Authors: Geraint H M Davies; Gary A Molander
Journal: J Org Chem Date: 2016-04-12 Impact factor: 4.354