Literature DB >> 29314835

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

Zachary X Giustra1, Shih-Yuan Liu1.   

Abstract

Boron-nitrogen heteroarenes hold great promise for practical application in many areas of chemistry. Enduring interest in realizing this potential has in turn driven perennial innovation with respect to these compounds' synthesis. This Perspective discusses in detail the most recent advances in methods pertaining to the preparation of BN-isosteres of benzene, naphthalene, and their derivatives. Additional focus is placed on the progress enabled by these syntheses toward functional utility of such BN-heterocycles in biochemistry and pharmacology, materials science, and transition-metal-based catalysis. The prospects for future research efforts in these and related fields are also assessed.

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Year:  2018        PMID: 29314835      PMCID: PMC6190836          DOI: 10.1021/jacs.7b09446

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  53 in total

1.  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

2.  Aromaticity and stability of azaborines.

Authors:  Marija Baranac-Stojanović
Journal:  Chemistry       Date:  2014-10-21       Impact factor: 5.236

3.  BN/CC isosterism in borazaronaphthalenes towards phosphodiesterase 10A (PDE10A) inhibitors.

Authors:  Alexandru Vlasceanu; Mikkel Jessing; John Paul Kilburn
Journal:  Bioorg Med Chem       Date:  2015-06-15       Impact factor: 3.641

4.  Formation of BN Isosteres of Azo Dyes by Ring Expansion of Boroles with Azides.

Authors:  Holger Braunschweig; Mehmet Ali Celik; Florian Hupp; Ivo Krummenacher; Lisa Mailänder
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-25       Impact factor: 15.336

5.  Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.

Authors:  Senmiao Xu; Yuanzhe Zhang; Bo Li; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2016-11-01       Impact factor: 15.419

6.  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

7.  Conversion of alkyltrifluoroborates into alkyldichloroboranes with tetrachlorosilane in coordinating solvents.

Authors:  Byung Ju Kim; Donald S Matteson
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-07       Impact factor: 15.336

8.  Synthesis of Functionalized 1,4-Azaborinines by the Cyclization of Di-tert-butyliminoborane and Alkynes.

Authors:  Marius Schäfer; Nicholas A Beattie; K Geetharani; Julian Schäfer; William C Ewing; Mirjam Krahfuß; Christian Hörl; Rian D Dewhurst; Stuart A Macgregor; Christoph Lambert; Holger Braunschweig
Journal:  J Am Chem Soc       Date:  2016-06-27       Impact factor: 15.419

9.  Accessing 2-(hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: palladium-catalyzed cross-couplings of 2-(chloromethyl)-2,1-borazaronaphthalenes.

Authors:  Gary A Molander; Javad Amani; Steven R Wisniewski
Journal:  Org Lett       Date:  2014-11-03       Impact factor: 6.005

10.  Reductive cross-coupling of 3-bromo-2,1-borazaronaphthalenes with alkyl iodides.

Authors:  Gary A Molander; Steven R Wisniewski; Kaitlin M Traister
Journal:  Org Lett       Date:  2014-06-30       Impact factor: 6.005

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  26 in total

1.  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

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.  3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

Authors:  Jordan S Compton; Borna Saeednia; Christopher B Kelly; Gary A Molander
Journal:  J Org Chem       Date:  2018-07-10       Impact factor: 4.354

4.  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

5.  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

6.  Exploring the strength of a hydrogen bond as a function of steric environment using 1,2-azaborine ligands and engineered T4 lysozyme receptors.

Authors:  Yao Liu; Shih-Yuan Liu
Journal:  Org Biomol Chem       Date:  2019-07-16       Impact factor: 3.876

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

Authors:  Klara Edel; Jacob S A Ishibashi; Shih-Yuan Liu; Holger F Bettinger
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-20       Impact factor: 15.336

8.  Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes.

Authors:  Xie Wang; Geraint H M Davies; Adriel Koschitzky; Steven R Wisniewski; Christopher B Kelly; Gary A Molander
Journal:  Org Lett       Date:  2019-03-27       Impact factor: 6.005

9.  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

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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