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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.)

Synthesis of (Z)-beta-halo alpha,beta-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid

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Author(s):
da Silva, Vitor A. F. [1] ; da Silva, Gustavo P. [1] ; Matsuo, Bianca T. [1] ; Ali, Akbar [1, 2] ; Davis, Rebecca L. [3] ; Zukerman-Schpector, Julio [1] ; Correa, Arlene G. [1] ; Paixao, Marcio W. [1]
Total Authors: 8
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Dept Chem, Ctr Excellence Res Sustainable Chem CERSusChem, Sao Carlos, SP - Brazil
[2] Univ Sargodha, Dept Chem, Sargodha 40100 - Pakistan
[3] Univ Manitoba, Dept Chem, Winnipeg, MB - Canada
Total Affiliations: 3
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 17, n. 3, p. 519-526, JAN 21 2019.
Web of Science Citations: 4
Abstract

A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (BrOnsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)--halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent. (AU)

FAPESP's process: 16/14560-6 - Combination of organocatalytic and multicomponent reactions in the assymetric synthesis of substituted tetrahydroquinolines
Grantee:Vitor Alcantara Fernandes da Silva
Support type: Scholarships in Brazil - Master
FAPESP's process: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
Grantee:Ricardo Samuel Schwab
Support type: Regular Research Grants
FAPESP's process: 16/12622-4 - Asymmetric Counteranion-Directed Organocatalysis: Synthesis of Heterocyclic Systems and Peptides Functionalization
Grantee:Márcio Weber Paixão
Support type: Scholarships abroad - Research
FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support type: Research Grants - Research Centers in Engineering Program