Literature DB >> 29989812

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

Jordan S Compton1, Borna Saeednia1, Christopher B Kelly1, Gary A Molander1.   

Abstract

A Pd-catalyzed Miyaura n class="Chemical">borylation of 3-bromo-2,1-borazaronaphthalenes is reported. This method allows the formation of umpolung reagents for subsequent Pd-mediated cross-coupling. Coupling of this nucleophilic partner with a variety of commercially available aryl- and heteroaryl halides allows facile and rapid diversification of these cores.

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Year:  2018        PMID: 29989812      PMCID: PMC6097885          DOI: 10.1021/acs.joc.8b01197

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  17 in total

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5.  Innocent BN bond substitution in anthracene derivatives.

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Journal:  Org Biomol Chem       Date:  2016-03-28       Impact factor: 3.876

6.  A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

Authors:  Steven R Wisniewski; Courtney L Guenther; O Andreea Argintaru; Gary A Molander
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

7.  Enantioselective synthesis of cyclic secondary amines through Mo-catalyzed asymmetric ring-closing metathesis (ARCM).

Authors:  Sarah J Dolman; Richard R Schrock; Amir H Hoveyda
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8.  Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

Authors:  Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

9.  Benzazaborinines as Novel Bioisosteric Replacements of Naphthalene: Propranolol as an Example.

Authors:  Frederik J R Rombouts; Fulgencio Tovar; Nigel Austin; Gary Tresadern; Andrés A Trabanco
Journal:  J Med Chem       Date:  2015-11-30       Impact factor: 7.446

10.  Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C-H Activation.

Authors:  Geraint H M Davies; Matthieu Jouffroy; Fatemeh Sherafat; Borna Saeednia; Casey Howshall; Gary A Molander
Journal:  J Org Chem       Date:  2017-07-17       Impact factor: 4.354

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  3 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.  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

3.  Selectivity in the Elaboration of Bicyclic Borazarenes.

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Journal:  Adv Synth Catal       Date:  2020-12-23       Impact factor: 5.837

  3 in total

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