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Molecules 2016, 21(11), 1539; doi:10.3390/molecules21111539

A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst

Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
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Academic Editor: Wei Zhang
Received: 1 September 2016 / Revised: 31 October 2016 / Accepted: 1 November 2016 / Published: 16 November 2016
(This article belongs to the Section Green Chemistry)
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Abstract

Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles. View Full-Text
Keywords: potassium allyltrifluoroborate; mechanochemistry; selectivity; alcohols; catalysis; lanthanide potassium allyltrifluoroborate; mechanochemistry; selectivity; alcohols; catalysis; lanthanide
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MDPI and ACS Style

de Souza, V.P.; Oliveira, C.K.; de Souza, T.M.; Menezes, P.H.; Alves, S.; Longo, R.L.; Malvestiti, I. A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst. Molecules 2016, 21, 1539.

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