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Mechanistic studies of Heck-Matsuda reactions: a theoretical investigation

Grant number: 13/04813-6
Support type:Scholarships in Brazil - Doctorate
Effective date (Start): March 01, 2014
Effective date (End): August 01, 2017
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Physical-Chemistry
Principal researcher:Ataualpa Albert Carmo Braga
Grantee:Vitor Hugo Menezes da Silva
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
Associated scholarship(s):15/11840-5 - Theoretical study on selectivity in Heck-Mizoroki reactions: comparisons between nickel and palladium catalytic systems, BE.EP.DR


The main goal of this project is the detailed theoretical study of the Heck-Matsuda reactions. As key topics we propose an investigation of an alternative mechanism for the oxidative addition step and the elucidation of which aspects control the enantioselectivity of such reactions. The methodology will be based on DFT calculations using pure and hybrid functionals. The insight obtained by these studies may provide the knowledge necessary to improve the current experimental protocols of Heck-Matsuda reactions. (AU)

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Scientific publications (9)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
MENEZES DA SILVA, VITOR H.; MORGON, NELSON H.; CORREIA, CARLOS R. D.; BRAGA, ATAUALPA A. C. DFT perspective on the selectivity and mechanism of ligand-free Heck reaction involving allylic esters and arenediazonium salts. JOURNAL OF ORGANOMETALLIC CHEMISTRY, v. 896, p. 5-15, SEP 15 2019. Web of Science Citations: 1.
MENEZES DA SILVA, VITOR H.; DE LIMA BATISTA, ANA PAULA; NAVARRO, OSCAR; BRAGA, ATAUALPA A. C. Theoretical study on selectivity trends in (N-heterocyclic carbene)-Pd catalyzed mizoroki-heck reactions: Exploring density functionals methods and molecular models. Journal of Computational Chemistry, v. 38, n. 28, p. 2371-2377, OCT 30 2017. Web of Science Citations: 4.
MENEZES DA SILVA, VITOR H.; MONEZI, NATALIA M.; ANDO, ROMULO A.; BRAGA, ATAUALPA A. C. New insights into the electrophilic aromatic substitution mechanism of tricyanovinylation reaction involving tetracyanoethylene and N,N-dimethylaniline: An interpretation based on density functional theory calculations. Journal of Molecular Structure, v. 1142, p. 58-65, AUG 15 2017. Web of Science Citations: 0.
VASCONCELOS, STANLEY N. S.; MENEZES DA SILVA, VITOR H.; BRAGA, ATAUALPA A. C.; SHAMIM, ANWAR; SOUZA, FREDERICO B.; PIMENTA, DANIEL C.; STEFANI, HELIO A. 3-Alkenyltyrosines Accessed by Suzuki-Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions. ASIAN JOURNAL OF ORGANIC CHEMISTRY, v. 6, n. 7, p. 913-920, JUL 2017. Web of Science Citations: 3.
MENEZES DA SIVA, VITOR H.; BRAGA, ATAUALPA A. C.; CUNDARI, THOMAS R. N-Heterocyclic Carbene Based Nickel and Palladium Complexes: A DFT Comparison of the Mizoroki-Heck Catalytic Cycles. Organometallics, v. 35, n. 18, p. 3170-3181, SEP 26 2016. Web of Science Citations: 14.
MENEZES DA SILVA, VITOR H.; SILVA, JR., LUIZ F.; BRAGA, ATAUALPA A. C. Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes: Mechanistic Insight by Computational Investigations. CHEMISTRYSELECT, v. 1, n. 11, p. 2706-2711, JUL 16 2016. Web of Science Citations: 2.
SILVA, JULIANA DE OLIVEIRA; ANGNES, RICARDO A.; MENEZES DA SILVA, VITOR H.; SERVILHA, BRUNO M.; ADEEL, MUHAMMAD; BRAGA, ATAUALPA A. C.; APONICK, AARON; CORREIA, CARLOS ROQUE D. Intermolecular Noncovalent Hydroxy-Directed Enantioselective Heck Desymmetrization of Cyclopentenol: Computationally Driven Synthesis of Highly Functionalized cis-4-Arylcyclopentenol Scaffolds. Journal of Organic Chemistry, v. 81, n. 5, p. 2010-2018, MAR 4 2016. Web of Science Citations: 25.
ANSELL, MELVYN B.; DA SILVA, VITOR H. MENEZES; HEERDT, GABRIEL; BRAGA, ATAUALPA A. C.; SPENCER, JOHN; NAVARRO, OSCAR. An experimental and theoretical study into the facile, homogenous (N-heterocyclic carbene)(2)-Pd(0) catalyzed diboration of internal and terminal alkynes. CATALYSIS SCIENCE & TECHNOLOGY, v. 6, n. 20, p. 7461-7467, 2016. Web of Science Citations: 11.
GUEST, DANIEL; MENEZES DA SILVA, VITOR H.; DE LIMA BATISTA, ANA P.; ROE, S. MARK; BRAGA, ATAUALPA A. C.; NAVARRO, OSCAR. (N-Heterocyclic Carbene)-Palladate Complexes in Anionic Mizoroki-Heck Coupling Cycles: A Combined Experimental and Computational Study. Organometallics, v. 34, n. 11, p. 2463-2470, JUN 8 2015. Web of Science Citations: 35.
Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
SILVA, Vitor Hugo Menezes da. Transition metal-catalyzed cross-coupling Heck reactions: A mechanistic study based on Density Functional Theory. 2017. Doctoral Thesis - Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ) São Paulo.

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