Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions

• Grant number: 12/00424-2
• Support Opportunities: Research Projects - Thematic Grants
• Start date: August 01, 2012
• End date: November 30, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Helio Alexandre Stefani
• Grantee: Helio Alexandre Stefani
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Associated researchers: Ignez Caracelli ; Julio Zukerman Schpector ; Sandra Helena Poliselli Farsky
• Associated scholarship(s): 16/05260-9 - Synthesis and functionalization of vinyl iodide sulfoxides, BP.DD; 13/21925-2 - 2-Aryl/Heteroaryloxazolines: Synthesis, Biological Activity and Fluorescence., BP.PD; 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts, BP.DR; 13/20553-4 - Synthesis and functionalization of vinyl iodide sulfoxides, BP.DD; 12/17954-4 - Cyclization reaction of Acetyl- and Ethylpyrrolidin-2-one with Potassium Organotrifluoroborate Salts, BP.PD

Abstract

The project's main theme, but not exclusively, is the use of potassium organotrifluoroborate salts (nucleophilic species) in the formation of carbon-carbon bond (sp2-sp2 bonds, sp2-sp, sp-sp) with organic halides and unsaturated species tellurium (electrophilic species), the latter as an alternative to traditional organic halides, catalyzed by transition metal complexes. Aims at the development of Suzuki-Miyaura type reactions that are viable, or other use of this class of reagents, is achieve small libraries of compounds for biological testing. (AU)

Scientific publications

(35)

(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)

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. (13/17960-7, 12/00424-2, 15/01491-3, 13/04813-6, 15/11840-5)

DE OLIVEIRA, ISADORA M.; VASCONCELOS, STANLEY S. N.; BARBEIRO, CRISTIANE S.; CORRERA, THIAGO C.; SHAMIM, ANWAR; PIMENTA, DANIEL C.; CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.; MANARIN, FLAVIA. Ytterbium(III)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines. NEW JOURNAL OF CHEMISTRY, v. 41, n. 18, p. 9884-9888, SEP 21 2017. (13/17960-7, 12/00424-2, 14/15962-5, 16/04289-3)

VASCONCELOS, STANLEY N. S.; BARBEIRO, CRISTIANE S.; KHAN, AMNA N.; STEFANI, HELIO A.. Synthesis of Biphenyl Tyrosine Via Cross-Coupling Suzuki-Miyaura Reaction Using Aryltrifluoroborate Salts. Journal of the Brazilian Chemical Society, v. 26, n. 4, p. 765-774, APR 2015. (13/17960-7, 12/00424-2)

CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; MADUREIRA, LUCAS SOUSA; MAGANHI, STELLA H.; STEFANI, HELIO A.; GUADAGNIN, RAFAEL C.; TIEKINK, EDWARD R. T.. Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, v. 231, n. 6, p. 321-328, JUN 2016. (12/00424-2, 12/22524-9)

ZUKERMAN-SCHPECTOR, JULIO; MADUREIRA, LUCAS SOUSA; STEFANI, HELIO A.; GOZHINA, OLGA; TIEKINK, EDWARD R. T.. Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, v. 231, n. 6, p. 329-339, JUN 2016. (12/00424-2)

SOUZA, FREDERICO B.; SHAMIM, ANWAR; ARGOMEDO, LUIZ M. Z.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of enyne and aryl vinyl sulfoxides: functionalization via Pummerer rearrangement. MOLECULAR DIVERSITY, v. 19, n. 4, p. 773-785, NOV 2015. (13/20553-4, 12/00424-2, 11/11499-0)

SHAMIM, ANWAR; VASCONCELOS, STANLEY N. S.; ALI, BAKHAT; MADUREIRA, LUCAS SOUSA; ZUKERMAN-SCHPECTOR, J.; STEFANI, HELIO A.. Ligand and copper free Sonogashira coupling to achieve 2-alkynyl D-glucal derivatives: regioselective electrophile promoted nucleophilic 5-endo-dig cyclization. Tetrahedron Letters, v. 56, n. 43, p. 5836-5842, OCT 21 2015. (12/00424-2)

KHAN, AMNA N.; VASCONCELOS, STANLEY N. S.; CARRAU, GONZALO; STEFANI, HELIO A.. Microwave-Assisted Synthesis of beta-1,2,3-Triazolyl-alpha-amino Esters. Journal of the Brazilian Chemical Society, v. 26, n. 7, p. 1457-1465, JUL 2015. (12/00424-2)

STEFANI, HELIO A.; MANARIN, FLAVIA; KHAN, AMNA N.; VASCONCELOS, STANLEY N. S.. Ytterbium(III)-Catalyzed Addition Reaction of Alkynyltrifluoroborate Salts to alpha-Imino Esters: Efficient Synthesis of beta-Unsaturated alpha-Amino Esters. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2014, n. 6, p. 1236-1240, FEB 2014. (12/00424-2)

ZUKERMAN-SCHPECTOR, JULIO; MADUREIRA, LUCAS SOUSA; WULF, GLAUDESTON DUTRA; STEFANI, HELIO A.; VASCONCELOS, STANLEY N. S.; NG, SEIK WENG; TIEKINK, EDWARD R. T.. Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers. Molecules, v. 19, n. 2, p. 1990-2003, FEB 2014. (12/00424-2)

STEFANI, HELIO A.; VASCONCELOS, STANLEY N. S.; MANARIN, FLAVIA; LEAL, DAIANA M.; SOUZA, FREDERICO B.; MADUREIRA, LUCAS SOUSA; ZUKERMAN-SCHPECTOR, JULIO; EBERLIN, MARCOS N.; GODOI, MARLA N.; GALAVERNA, RENAN DE SOUZA. Synthesis of 5-Organotellanyl-1H-1,2,3-triazoles: Functionalization of the 5-Position Scaffold by the Sonogashira Cross-Coupling Reaction. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2013, n. 18, p. 3780-3785, JUN 2013. (12/00424-2, 10/15677-8)

SHAMIM, ANWAR; SOUZA, FREDERICO B.; TROSSINI, GUSTAVO H. G.; GATTI, FERNANDO M.; STEFANI, HELIO A.. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal. MOLECULAR DIVERSITY, v. 19, n. 3, p. 423-434, AUG 2015. (13/20553-4, 12/00424-2)

SHAMIM, ANWAR; SOUZA, FREDERICO B.; VASCONCELOS, STANLEY N. S.; STEFANI, HELIO A.. Synthesis of a library of glucal-derived triazoles via copper-catalyzed azide-alkyne cyclization. Tetrahedron Letters, v. 58, n. 9, p. 884-888, MAR 1 2017. (12/00424-2)

VASCONCELOS, STANLEY N. S.; SHAMIM, ANWAR; ALI, BAKHAT; DE OLIVEIRA, ISADORA M.; STEFANI, HELIO A.. Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine. MOLECULAR DIVERSITY, v. 20, n. 2, p. 469-481, MAY 2016. (13/17960-7, 12/00424-2)

VASCONCELOS, STANLEY N. S.; DREWES, CARINE C.; KANDA KUPA, LEONARD DE VINCI; FARSKY, SANDRA H. P.; STEFANI, HELIO A.. Evaluation of toxicity on epithelial and tumor cells of biaryl dipeptide tyrosines. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 114, p. 1-7, MAY 23 2016. (13/17960-7, 12/00424-2, 10/19802-1)

VASCONCELOS, STANLEY N. S.; MEISSNER, KAMILA A.; FERRAZ, WITOR R.; TROSSINI, GUSTAVO H. G.; WRENGER, CARSTEN; STEFANI, HELIO A.. Indole-3-glyoxyl tyrosine: synthesis and antimalarial activity against Plasmodium falciparum. Future Medicinal Chemistry, v. 11, n. 6, p. 525-538, MAR 2019. (13/17960-7, 12/12807-3, 15/26722-8, 12/00424-2, 17/25543-8, 16/24790-9)

SOUZA, FREDERICO B.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Microwave-assisted one-pot three-component synthesis of imine 1,2,3-triazoles. Tetrahedron Letters, v. 57, n. 14, p. 1592-1596, APR 6 2016. (13/20553-4, 12/00424-2)

AMNA N. KHAN; STANLEY N. S. VASCONCELOS; GONZALO CARRAU; HÉLIO A. STEFANI. Microwave-Assisted Synthesis of β-1,2,3-Triazolyl-α-amino Esters. Journal of the Brazilian Chemical Society, v. 26, n. 7, p. 1457-1465, 2015-07-00. (12/00424-2)

VASCONCELOS, STANLEY N. S.; FORNARI, EVELIN; CARACELLI, IGNEZ; STEFANI, HELIO A.. Synthesis of alpha-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles. MOLECULAR DIVERSITY, v. 21, n. 4, p. 893-902, NOV 2017. (13/17960-7, 12/00424-2)

SHAMIM, ANWAR; VASCONCELOS, STANLEY N. S.; DE OLIVEIRA, ISADORA MARIA; REIS, JOEL S.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.. Synthesis of Glycosyl Azides and Their Applications Using CuAAC Click Chemistry to Generate Bis- and Tris(triazolyl)glycosyl Derivatives. SYNTHESIS-STUTTGART, v. 49, n. 23, p. 5183-5196, DEC 2017. (12/00424-2)

SHAMIM, ANWAR; BARBEIRO, CRIATIANE S.; ALI, BAKHAT; STEFANI, HELIO A.. Synthesis of Stannyl-Substituted D-Glucal Derivatives via Palladium-Catalyzed Regioselective Hydrostannation and Their Synthetic Applications. CHEMISTRYSELECT, v. 1, n. 18, p. 5653-5659, NOV 1 2016. (12/00424-2, 12/17954-4)

SOUZA, FREDERICO B.; VASCONCELOS, STANLEY N. S.; REIS, JOEL S.; PIMENTA, DANIEL C.; STEFANI, HELIO. Synthesis and functionalization of N-sulfinyl imines: Sonogashira reaction and copper-catalyzed azide-alkyne cycloaddition. Tetrahedron Letters, v. 58, n. 11, p. 1057-1060, MAR 15 2017. (12/00424-2, 16/05260-9)

BALFOUR, MICHAEL N.; FRANCO, CAIO H.; MORAES, CAROLINA B.; FREITAS-JUNIOR, LUCIO H.; STEFANI, HELIO A.. Synthesis and trypanocidal activity of a library of 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 128, p. 202-212, MAR 10 2017. (12/00424-2)

VASCONCELOS, STANLEY N. S.; BELTRAN RODRIGUES, ANA CLARA; BASTOS, ERICK LEITE; STEFANI, HELIO A.. Synthesis of a Tyr-Tyr Peptide Library and Fluorescence of the Stilbenyl Derivatives. CHEMISTRYSELECT, v. 1, n. 6, p. 1287-1291, MAY 1 2016. (14/14866-2, 12/00424-2, 13/17960-7)

ALI, BAKAT; KUPA, LEONARD D. KANDA; HELUANY, CINTIA S.; DREWES, CARINE C.; VASCONCELOS, STANLEY N. S.; FARSKY, SANDRA H. P.; STEFANI, HELIO A.. Cytotoxic effects of a novel maleimide derivative on epithelial and tumor cells. BIOORGANIC CHEMISTRY, v. 72, p. 199-207, JUN 2017. (13/17960-7, 12/17954-4, 12/00424-2, 10/19802-1, 14/07328-4)

ALI, BAKHAT; VASCONCELOS, STANLEY N. S.; SHAMIM, ANWAR; ZUKERMAN-SCHPECTOR, J.; STEFANI, HELIO A.. Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones and functionalization to triazoles. ARABIAN JOURNAL OF CHEMISTRY, v. 10, n. 4, p. 500-508, MAY 2017. (12/00424-2, 12/17954-4, 13/17960-7)

STEFANI, HELIO A.; FERREIRA, FERNANDO P.; ALI, BAKHAT; PIMENTA, DANIEL C.. Synthesis of functionalized N-triazolyl maleimides. Tetrahedron Letters, v. 55, n. 31, p. 4355-4358, JUL 30 2014. (12/00424-2, 12/17954-4)

STEFANI, HELIO A.; MANARIN, FLAVIA; SOUSA, ARIANE C. S.; SOUZA, FREDERICO B.; FERRAZ, WITOR RIBEIRO. Three-component reaction for the synthesis of diverse beta-unsaturated alpha-amino esters. Tetrahedron, v. 70, n. 20, p. 3243-3248, MAY 20 2014. (12/00424-2)

ALI, BAKHAT; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, FERNANDO P.; SHAMIM, ANWAR; PIMENTA, DANIEL C.; STEFANI, HELICI A.. Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes. Tetrahedron Letters, v. 56, n. 9, p. 1153-1158, FEB 25 2015. (12/00424-2, 12/17954-4, 11/11499-0)

ALI, BAKHAT; SHAMIM, ANWAR; VASCONCELOS, STANLEY N. S.; STEFANI, HELIO A.. Synthesis and applications of 4-substituted 1-(4-iodophenyl)pyrrolidine-2,5-diones. Tetrahedron Letters, v. 56, n. 28, p. 4234-4241, JUL 8 2015. (12/00424-2, 12/17954-4)

STEFANI, HELIO A.; KHAN, AMNA N.; MANARIN, FLAVIA; VENDRAMINI, PEDRO H.; EBERLIN, MARCOS N.. Synthesis of alpha-alkenyl-alpha-amino esters via addition of potassium Alkenyltrifluoroborate salts to imine in the presence of Yb(OTf)(3). Tetrahedron Letters, v. 54, n. 46, p. 6204-6207, NOV 13 2013. (12/00424-2, 10/15677-8)

STEFANI, HELIO A.; VASCONCELOS, STANLEY N. S.; SOUZA, FREDERICO B.; MANARIN, FLAVIA; ZUKERMAN-SCHPECTOR, JULIO. One-pot three-component synthesis of indole-3-glyoxyl derivatives and indole-3-glyoxyl triazoles. Tetrahedron Letters, v. 54, n. 43, p. 5821-5825, OCT 23 2013. (12/00424-2)

STEFANI, HELIO A.; ALI, BAKHAT; FERREIRA, FERNANDO P.. Ultrasound-assisted addition of alcohols to N-acyliminium ions mediated by In(OTf)3 and synthesis of 1,2,3-triazoles. Tetrahedron Letters, v. 55, n. 23, p. 3400-3405, JUN 4 2014. (12/00424-2, 12/17954-4)

STEFANI, HELIO A.; SILVA, NATHALIA C. S.; VASCONCELOS, STANLEY N. S.; MANARIN, FLAVIA; SOUZA, FREDERICO B.. Functionalization of 5-telluro-1,2,3-triazoles: Te/Li exchange and Suzuki-Miyaura cross-coupling reaction. Tetrahedron Letters, v. 54, n. 22, p. 2809-2812, MAY 29 2013. (12/00424-2, 10/15677-8)

ZUKERMAN-SCHPECTOR, JULIO; CARACELLI, I.; STEFANI, HELIO A.; KHAN, AMNA N.; TIEKINK, EDWARD R. T.. Crystal structure of ethyl 2-[(4-bromophenyl) amino]-3,4-dimethylpent- 3enoate. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, v. 70, p. 12-pg., 2014-10-01. (12/00424-2)