A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst
Viviane P. de Souza,
Cristiane K. Oliveira,
Thiago M. de Souza,
Paulo H. Menezes,
Severino Alves,
Ricardo L. Longo,
Ivani Malvestiti
Affiliations
Viviane P. de Souza
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
Cristiane K. Oliveira
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
Thiago M. de Souza
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
Paulo H. Menezes
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
Severino Alves
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
Ricardo L. Longo
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
Ivani Malvestiti
Departamento de Química Fundamental—Universidade Federal de Pernambuco, Av. Jornalista Aníbal Fernandes, s/n—Cidade Universitária, Recife—PE 50740-560, Brazil
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.
