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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates

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Author(s):
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]
Total Authors: 7
Affiliation:
[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
Total Affiliations: 7
Document type: Journal article
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2019, n. 22, p. 3560-3566, JUN 16 2019.
Web of Science Citations: 1
Abstract

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)

FAPESP's process: 14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy
Grantee:Thiago Carita Correra
Support Opportunities: Research Grants - Young Investigators Grants
FAPESP's process: 15/08539-1 - Multi-User Equipment approved in grant 2014/15962-5: ion trap mass spectrometer modified to perform infrared vibrational spectroscopy (IRMPD)
Grantee:Thiago Carita Correra
Support Opportunities: Multi-user Equipment Program