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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.)

3-Alkenyltyrosines Accessed by Suzuki-Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions

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Author(s):
Vasconcelos, Stanley N. S. ; Menezes da Silva, Vitor H. ; Braga, Ataualpa A. C. ; Shamim, Anwar ; Souza, Frederico B. ; Pimenta, Daniel C. ; Stefani, Helio A.
Total Authors: 7
Document type: Journal article
Source: ASIAN JOURNAL OF ORGANIC CHEMISTRY; v. 6, n. 7, p. 913-920, JUL 2017.
Web of Science Citations: 3
Abstract

3-Vinyl and 3-stilbenyl tyrosine derivatives, accessed by the Suzuki-Miyaura coupling reaction in good yields, are presented. These synthetic olefins then provided a fast and effective synthesis of functionalized quinolines by a silver-catalyzed, microwave-mediated Povarov reaction in just 40min. In addition, we demonstrate a tandem one-pot microwave-mediated Povarov-CuAAC (copper-catalyzed azide-alkyne cycloaddition) synthesis to provide a 1,2,3-triazole ring with 35% overall yield. We propose a Povarov/aromatization mechanism, based on high-resolution mass spectrometry experiments, combined with computational studies based on density functional theory (DFT) methods. (AU)

FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
Grantee:Ataualpa Albert Carmo Braga
Support type: Regular Research Grants
FAPESP's process: 13/04813-6 - Mechanistic studies of Heck-Matsuda reactions: a theoretical investigation
Grantee:Vitor Hugo Menezes da Silva
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts
Grantee:Stanley Nunes Siqueira Vasconcelos
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 15/11840-5 - Theoretical study on selectivity in Heck-Mizoroki reactions: comparisons between nickel and palladium catalytic systems
Grantee:Vitor Hugo Menezes da Silva
Support type: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
Grantee:Helio Alexandre Stefani
Support type: Research Projects - Thematic Grants