Clean protocol for deoxygenation of epoxides to alkenes via catalytic hydrogenation using gold

Autor(es)

Fiorio, Jhonatan L. ^[1] ; Rossi, Liane M. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: CATALYSIS SCIENCE & TECHNOLOGY; v. 11, n. 1, p. 312-318, JAN 7 2021.
• Citações Web of Science: 0

Resumo

The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)(3) is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. (AU)

• Processo FAPESP: 16/16738-7 - Estudo da influência de ligantes orgânicos sobre a reatividade de nanopartículas de ouro
• Beneficiário: Liane Marcia Rossi
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 18/26253-6 - Catálise cooperativa: uma alternativa para o desenvolvimento de catalisadores a base de ouro e metais de transição abundantes
• Beneficiário: Liane Marcia Rossi
• Modalidade de apoio: Auxílio à Pesquisa - Regular