The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates

Autor(es)

Tripodi, Guilherme L. ^[1] ; Correra, Thiago C. ^[2] ; Angolini, Celio F. F. ^[3] ; Ferreira, Bruno R. V. ^[4] ; Maitre, Philippe ^[5] ; Eberlin, Marcos N. ^{[6, 7]} ; Roithova, Jana ^[1]

Afiliação do(s) autor(es)

^[1] Radboud Univ Nijmegen, Inst Mol & Mat, Heyendaalseweg 135, NL-6525 AJ Nijmegen - Netherlands

^[2] Univ Sao Paulo, Inst Chem, Dept Organ Chem, BR-05508000 Sao Paulo, SP - Brazil

^[3] Fed Univ ABC UFABC, Ctr Nat & Human Sci, BR-09210580 Santo Andre, SP - Brazil

^[4] Inst Fed Norte Minas Gerais, Campus Salinas, BR-39560000 Salinas, MG - Brazil

^[5] Univ Paris Saclay, Univ Paris Sud, CNRS, Lab Chim Phys, URM8000, F-91405 Orsay - France

^[6] Univ Estadual Campinas, Inst Chem, Thomson Mass Spectrometry Lab, BR-13084971 Campinas, SP - Brazil

^[7] Mackenzie Presbiterian Univ, Sch Engn, BR-01302907 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2019, n. 22, p. 3560-3566, JUN 16 2019.
• Citações Web of Science: 1

Resumo

Lanthanide triflates are effective Lewis acid catalysts in reactions involving carbonyl compounds due to their high oxophilicity and water stability. Despite the growing interest, the identity of the catalytic species formed in lanthanide catalysed reactions is still unknown. We have therefore used mass spectrometry and ion spectroscopy to intercept and characterize the intermediates in a reaction catalysed by ytterbium and dysprosium triflates. We were able to identify a number of lanthanide intermediates formed in a simple condensation reaction between a C-acid and an aldehyde. Results show correlation between the reactivity of lanthanide complexes and their charge state and suggest that the triply charged complexes play a key role in lanthanide catalysed reactions. Spectroscopic data of the gaseous ions accompanied by theoretical calculations reveal that the difference between catalytic efficiencies of ytterbium and dysprosium ions can be explained by their different electrophilicity. (AU)

• Processo FAPESP: 14/15962-5 - Mecanismos de reação de sistemas catalíticos assimétricos por espectrometria de massas e espectroscopia vibracional de íons na fase gasosa
• Beneficiário: Thiago Carita Correra
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 15/08539-1 - EMU concedido no processo 2014/15962-5: espectrômetro de massas tipo íon TRAP modificado para realização de espectroscopia vibracional no infravermelho (IRMPD)
• Beneficiário: Thiago Carita Correra
• Modalidade de apoio: Auxílio à Pesquisa - Programa Equipamentos Multiusuários