Literature DB >> 17263583

A practical synthesis of alpha-aryl methyl ketones via a transition-metal-free Meerwein arylation.

Carmela Molinaro1, Jeffrey Mowat, Francis Gosselin, Paul D O'Shea, Jean-François Marcoux, Rémy Angelaud, Ian W Davies.   

Abstract

We report herein a simple, scalable, transition-metal-free approach to the synthesis of alpha-aryl methyl ketones from diazonium tetrafluoroborate salts under mild conditions. This methodology uses easily accessible and nontoxic starting material and was applied to the multi-kilogram-scale preparation of 1-(3-bromo-4-methylphenyl)propan-2-one.

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Year:  2007        PMID: 17263583     DOI: 10.1021/jo062483g

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


  8 in total

1.  Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity.

Authors:  Seth Daly; Kathryn Hayden; Indranil Malik; Nikki Porch; Hong Tang; Snezna Rogelj; Liliya V Frolova; Katrina Lepthien; Alexander Kornienko; Igor V Magedov
Journal:  Bioorg Med Chem Lett       Date:  2011-06-25       Impact factor: 2.823

2.  Gold Redox Catalysis through Base-Initiated Diazonium Decomposition toward Alkene, Alkyne, and Allene Activation.

Authors:  Boliang Dong; Haihui Peng; Stephen E Motika; Xiaodong Shi
Journal:  Chemistry       Date:  2017-07-24       Impact factor: 5.236

3.  Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes.

Authors:  George Iakobson; Junyi Du; Alexandra M Z Slawin; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2015-08-26       Impact factor: 2.883

4.  Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.

Authors:  Fei Zhou; Tom G Driver
Journal:  Org Lett       Date:  2014-05-27       Impact factor: 6.005

5.  Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts.

Authors:  Stephanie Kindt; Karina Wicht; Markus R Heinrich
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-08       Impact factor: 15.336

6.  Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone.

Authors:  Edson Leonardo Scarpa de Souza; Carson Wiethan; Carlos Roque Duarte Correia
Journal:  ACS Omega       Date:  2019-10-29

7.  2-Fluoro-5-nitrophenyldiazonium: A Novel Sanger-Type Reagent for the Versatile Functionalization of Alcohols.

Authors:  Oliver Fischer; Markus R Heinrich
Journal:  Chemistry       Date:  2021-02-24       Impact factor: 5.236

8.  Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling.

Authors:  Haihui Peng; Rong Cai; Chang Xu; Hao Chen; Xiaodong Shi
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825

  8 in total

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