Literature DB >> 19823745

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

Ashley N Lamm1, Shih-Yuan Liu.   

Abstract

The stability of 1,2-dihydro-1,2-azaborines toward oxygen and water was investigated as a function of their ring substituents: while generally 1,2-dihydro-1,2-azaborines are compatible with water, their stability toward oxygen is dependent on the boron and the C(3) substituents, and we found that electron withdrawing groups enhanced the heterocycle's ability to resist oxidative degradation.

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Year:  2009        PMID: 19823745     DOI: 10.1039/b904120f

Source DB:  PubMed          Journal:  Mol Biosyst        ISSN: 1742-2051


  11 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.  Boron in disguise: the parent "fused" BN indole.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-07-13       Impact factor: 15.419

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

Authors:  Ashley N Lamm; Edward B Garner; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       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.  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

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.  A 1,3-dihydro-1,3-azaborine debuts.

Authors:  Senmiao Xu; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-11-21       Impact factor: 15.419

8.  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

9.  Rhodium-catalyzed B-H activation of 1,2-azaborines: synthesis and characterization of BN isosteres of stilbenes.

Authors:  Alec N Brown; Lev N Zakharov; Tanya Mikulas; David A Dixon; Shih-Yuan Liu
Journal:  Org Lett       Date:  2014-06-11       Impact factor: 6.005

10.  Will 1,2-dihydro-1,2-azaborine-based drugs resist metabolism by cytochrome P450 compound I?

Authors:  Pedro J Silva
Journal:  PeerJ       Date:  2016-07-28       Impact factor: 2.984

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