One-Pot Synthesis of Benzopinacolone Derivatives from Acetophenones

Autor(es)

Meira, Andreia Joice O. ; de Queiroz, Thiago B. ; Omori, Alvaro T.

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 36, n. 1, p. 5-pg., 2025-01-01.

Resumo

Pinacolone and benzopinacolone derivatives are an important class of organic compounds due to their uses in polymer synthesis and more recently as biologically active compounds. The conventional synthesis of such molecules is generally done in two steps, the pinacol coupling followed by the pinacol/pinacolone rearrangement. Aiming to prepare benzopinacolone derivatives in a greener fashion, we present here a one-step synthesis from acetophenones in the presence of zinc and tert-butyl chloride. To develop the methodology, conditions to prepare 3,3-diphenyl-2-butanone from acetophenone were optimized. To assess the scope, different substituted acetophenones were tested, resulting in the corresponding benzopinacolones at moderate yields (20-50%) with high purity. Structural elucidations were performed by H-1 and C-13 NMR (nuclear magnetic resonance spectroscopy) and GC-MS (gas chromatography-mass spectrometry). (AU)

• Processo FAPESP: 21/13573-5 - Metodologias alternativas na síntese de medicamentos para intubação e do Molnupiravir usando princípios da química circular e da química verde
• Beneficiário: Alvaro Takeo Omori
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 20/13466-1 - Design, síntese e caracterização de sistemas moleculares para colheita de luz e separação de cargas
• Beneficiário: Thiago Branquinho de Queiroz
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores