Literature DB >> 15200321

ipso-nitration of arylboronic acids with chlorotrimethylsilane-nitrate salts.

G K Surya Prakash1, Chiradeep Panja, Thomas Mathew, Vijayalakshmi Surampudi, Nicos A Petasis, George A Olah.   

Abstract

[reaction: see text] A mixture of nitrate salt and chlorotrimethylsilane is found to be an efficient regioselective nitrating agent for the ipso-nitration of arylboronic acids to produce the corresponding nitroarenes in moderate to excellent yields. High selectivity, simplicity, and convenience are the key features of the reaction.

Entities:  

Year:  2004        PMID： 15200321     DOI： 10.1021/ol0493249

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Metal-free chlorodeboronation of organotrifluoroborates.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2011-08-03       Impact factor: 4.354

2.  Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2012-04-24       Impact factor: 4.354

3.  Transition-Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives.

Authors:  Chen Zhu; John R Falck
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

4.  Electrochemical Nitration with Nitrite.

Authors:  Stephan P Blum; Christean Nickel; Lukas Schäffer; Tarik Karakaya; Siegfried R Waldvogel
Journal:  ChemSusChem       Date:  2021-10-22       Impact factor: 9.140

5.  Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.

Authors:  Brett P Fors; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

6.  Catalyst free, base free microwave irradiated synthesis of aryl nitrites from potassium aryltrifluoroborates and bismuth nitrate.

Authors:  Mohammad Al-Masum; Rebecca L Welch
Journal:  Tetrahedron Lett       Date:  2014-03-05       Impact factor: 2.415

7.  Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.

Authors:  Chen Zhu; Gongqiang Li; Daniel H Ess; John R Falck; László Kürti
Journal:  J Am Chem Soc       Date:  2012-10-25       Impact factor: 15.419

8.  One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts.

Authors:  Marcus Reitti; Piret Villo; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-08       Impact factor: 15.336

9.  Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin.

Authors:  Roxan Calvo; Kun Zhang; Alessandro Passera; Dmitry Katayev
Journal:  Nat Commun       Date:  2019-07-30       Impact factor: 14.919

10.  Electronically Driven Regioselective Iridium-Catalyzed C-H Borylation of Donor-π-Acceptor Chromophores Containing Triarylboron Acceptors.

Authors:  Florian Rauch; Johannes Krebs; Julian Günther; Alexandra Friedrich; Martin Hähnel; Ivo Krummenacher; Holger Braunschweig; Maik Finze; Todd B Marder
Journal:  Chemistry       Date:  2020-07-23       Impact factor: 5.236
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