Literature DB >> 25242828

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

Mohammad Al-Masum1, Rebecca L Welch1.   

Abstract

A mixture of bismuth nitrate pentahydrate and potassium aryltrifluoroborate in toluene under microwave heating at 120 °C for 20 min provides an interesting and mild reaction protocol for the synthesis of aryl nitrite. The conversion to aryl nitrites from aryltrifluoroborates without transition metal catalyst and base in high yields is remarkable.

Entities:  

Keywords:  Bismuth nitrate as nitrite source; Catalyst free reaction; Microwave; Potassium aryltrifluoroborates

Year:  2014        PMID: 25242828      PMCID: PMC4165087          DOI: 10.1016/j.tetlet.2014.01.102

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  7 in total

1.  Microwave-enhanced palladium-catalyzed cross-coupling reactions of potassium vinyltrifluoroborates and allyl acetates: a new route to 1,4-pentadienes.

Authors:  George W Kabalka; Mohammad Al-Masum
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

2.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

Review 3.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  A novel route to organonitrites by Pd-catalyzed cross-coupling of sodium nitrite and potassium organotrifluoroborates.

Authors:  Mohammad Al-Masum; Nabil Saleh; Tasfia Islam
Journal:  Tetrahedron Lett       Date:  2013-02-01       Impact factor: 2.415

5.  Highly efficient nitration of phenolic compounds in solid phase or solution using Bi(NO3)3.5H2O as nitrating reagent.

Authors:  Hong-Bin Sun; Ruimao Hua; Yingwu Yin
Journal:  J Org Chem       Date:  2005-10-28       Impact factor: 4.354

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

Authors:  G K Surya Prakash; Chiradeep Panja; Thomas Mathew; Vijayalakshmi Surampudi; Nicos A Petasis; George A Olah
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

7.  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

  7 in total

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