Literature DB >> 31134984

Late-stage functionalization of BN-heterocycles.

Cameron R McConnell1, Shih-Yuan Liu.   

Abstract

BN/CC isosterism has emerged as a viable strategy to expand the chemical space of organic molecules. In particular, the application of BN/CC isosterism to arenes has received significant attention due to the vast available chemical space provided by aromatic hydrocarbons. The synthetic efforts directed at assembling novel aromatic BN heterocycles have resulted in the discovery of new properties and functions in a variety of fields including biomedical research, medicinal chemistry, materials science, catalysis, and organic synthesis. This tutorial review specifically covers recent advances in synthetic technologies that functionalize assembled boron-nitrogen (BN) heterocycles and highlights their distinct reactivity and selectivity in comparison to their carbonaceous counterparts. It is intended to serve as a state-of-the-art compendium for readers who are interested in the reaction chemistry of BN heterocycles.

Entities:  

Year:  2019        PMID: 31134984      PMCID: PMC6609152          DOI: 10.1039/c9cs00218a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  36 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.  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

3.  Electrophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborines.

Authors:  Jun Pan; Jeff W Kampf; Arthur J Ashe
Journal:  Org Lett       Date:  2007-01-24       Impact factor: 6.005

4.  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

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.  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

8.  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

9.  A simple route to azaborinylphosphines: isoelectronic B-N analogues of arylphosphine ligands.

Authors:  Jonathan A Bailey; Mairi F Haddow; Paul G Pringle
Journal:  Chem Commun (Camb)       Date:  2014-02-11       Impact factor: 6.222

10.  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

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  12 in total

Review 1.  Merging Boron with Nitrogen-Oxygen Bonds: A Review on BON Heterocycles.

Authors:  Ivan S Golovanov; Alexey Yu Sukhorukov
Journal:  Top Curr Chem (Cham)       Date:  2021-02-05

2.  Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Authors:  Zachary X Giustra; Xinyu Yang; Min Chen; Holger F Bettinger; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

3.  Cation-π binding ability of BN indole.

Authors:  Katherine Boknevitz; Clovis Darrigan; Anna Chrostowska; Shih-Yuan Liu
Journal:  Chem Commun (Camb)       Date:  2020-03-31       Impact factor: 6.222

4.  The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Authors:  Yao Liu; Raimon Puig de la Bellacasa; Bo Li; Ana Belén Cuenca; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2021-08-25       Impact factor: 16.383

5.  Design and synthesis of stable four-coordinated benzotriazole-borane with tunable fluorescence emission.

Authors:  Qi Tang; Shi-Jun Li; Xiaohan Ye; Teng Yuan; Kai Zhao; Ying He; Chuan Shan; Lukasz Wojtas; David Richardson; Yu Lan; Xiaodong Shi
Journal:  Chem Sci       Date:  2022-04-18       Impact factor: 9.969

6.  NBN-Doped Bis-Tetracene and Peri-Tetracene: Synthesis and Characterization.

Authors:  Yubin Fu; Xiao Chang; Huan Yang; Evgenia Dmitrieva; Yixuan Gao; Ji Ma; Li Huang; Junzhi Liu; Hongliang Lu; Zhihai Cheng; Shixuan Du; Hong-Jun Gao; Xinliang Feng
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-05       Impact factor: 16.823

Review 7.  The Rise of 1,4-BN-Heteroarenes: Synthesis, Properties, and Applications.

Authors:  Cheng Chen; Cheng-Zhuo Du; Xiao-Ye Wang
Journal:  Adv Sci (Weinh)       Date:  2022-04-14       Impact factor: 17.521

8.  Enhanced N-directed electrophilic C-H borylation generates BN-[5]- and [6]helicenes with improved photophysical properties.

Authors:  Kang Yuan; Daniel Volland; Sven Kirschner; Marina Uzelac; Gary S Nichol; Agnieszka Nowak-Król; Michael J Ingleson
Journal:  Chem Sci       Date:  2022-01-04       Impact factor: 9.825

9.  BN-Embedded Perylenes.

Authors:  Xiangdong Fang
Journal:  Molecules       Date:  2021-11-25       Impact factor: 4.411

10.  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

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