Literature DB >> 17447777

Brønsted acid-catalyzed benzylation of 1,3-dicarbonyl derivatives.

Roberto Sanz1, Delia Miguel, Alberto Martínez, Julia M Alvarez-Gutiérrez, Félix Rodríguez.   

Abstract

The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Brønsted acids such as triflic acid (TfOH) and p-toluenesulfonic acid (PTS) to give rise to monoalkylated dicarbonyl derivatives in high yields. In the absence of the nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. The reactions are carried out in air using undried solvents, with water being the only side product of the process.

Entities:  

Year:  2007        PMID: 17447777     DOI: 10.1021/ol070624a

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


  2 in total

1.  A review of new developments in the Friedel-Crafts alkylation - From green chemistry to asymmetric catalysis.

Authors:  Magnus Rueping; Boris J Nachtsheim
Journal:  Beilstein J Org Chem       Date:  2010-01-20       Impact factor: 2.883

2.  Gram-Scale Synthesis of Flavoring Ketones in One Pot via Alkylation-Decarboxylation on Benzylic Carbon Using a Commercial Solid Acid Catalyst.

Authors:  Dhanaji R Naikwadi; Krishnan Ravi; Amravati S Singh; Jacky H Advani; Ankush V Biradar
Journal:  ACS Omega       Date:  2020-06-11
  2 in total

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