Literature DB >> 21751320

Nucleophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborine.

Ashley N Lamm1, Edward B Garner, David A Dixon, Shih-Yuan Liu.   

Abstract

Could go either way: the addition of nucleophiles to the parent 1,2-dihydro-1,2-azaborine and subsequent quenching with an electrophile generates novel substituted 1,2-azaborine derivatives. Mechanistic studies are consistent with two distinct nucleophilic aromatic substitution pathways depending on the nature of the nucleophile.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21751320      PMCID： PMC3437382          DOI： 10.1002/anie.201103192

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


  16 in total

1.  Microwave spectrum, structural parameters, and quadrupole coupling for 1,2-dihydro-1,2-azaborine.

Authors:  Adam M Daly; Chakree Tanjaroon; Adam J V Marwitz; Shih-Yuan Liu; Stephen G Kukolich
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

2.  A hybrid organic/inorganic benzene.

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

3.  Electrophilic aromatic substitution of a BN indole.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2010-11-02       Impact factor: 15.419

4.  How stable are 1,2-dihydro-1,2-azaborines toward water and oxygen?

Authors:  Ashley N Lamm; Shih-Yuan Liu
Journal:  Mol Biosyst       Date:  2009-08-10

5.  Hydrogen storage by boron-nitrogen heterocycles: a simple route for spent fuel regeneration.

Authors:  Patrick G Campbell; Lev N Zakharov; Daniel J Grant; David A Dixon; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

6.  1,2-Azaborine cations.

Authors:  Adam J V Marwitz; Jesse T Jenkins; Lev N Zakharov; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-04       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.  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

10.  Theoretical studies of borazynes and azaborines.

Authors:  Paul J Fazen; Luke A Burke
Journal:  Inorg Chem       Date:  2006-03-20       Impact factor: 5.165
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  13 in total

Review 1.  Recent advances in azaborine chemistry.

Authors:  Patrick G Campbell; Adam J V Marwitz; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-29       Impact factor: 15.336

2.  Late-stage functionalization of BN-heterocycles.

Authors:  Cameron R McConnell; Shih-Yuan Liu
Journal:  Chem Soc Rev       Date:  2019-07-01       Impact factor: 54.564

3.  Photoisomerization of 1,2-dihydro-1,2-azaborine: a matrix isolation study.

Authors:  Sarah A Brough; Ashley N Lamm; Shih-Yuan Liu; Holger F Bettinger
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-28       Impact factor: 15.336

4.  Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.

Authors:  Alec N Brown; Bo Li; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2015-07-09       Impact factor: 15.419

5.  UV-photoelectron spectroscopy of 1,2- and 1,3-azaborines: a combined experimental and computational electronic structure analysis.

Authors:  Anna Chrostowska; Senmiao Xu; Ashley N Lamm; Audrey Mazière; Christopher D Weber; Alain Dargelos; Patrick Baylère; Alain Graciaa; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2012-06-06       Impact factor: 15.419

6.  Rhodium-catalyzed boron arylation of 1,2-azaborines.

Authors:  Gabriel E Rudebusch; Lev N Zakharov; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

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

Authors:  Senmiao Xu; Tanya C Mikulas; Lev N Zakharov; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-07       Impact factor: 15.336

8.  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

9.  Protecting group-free synthesis of 1,2-azaborines: a simple approach to the construction of BN-benzenoids.

Authors:  Eric R Abbey; Ashley N Lamm; Andrew W Baggett; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

10.  A Boron Protecting Group Strategy for 1,2-Azaborines.

Authors:  Andrew W Baggett; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2017-10-11       Impact factor: 15.419
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