Jaqueline Senra | UERJ - Universidade do Estado do Rio de Janeiro / Rio de Janeiro State University (original) (raw)
Papers by Jaqueline Senra
Advanced Synthesis & Catalysis, 2009
... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible ... more ... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible sites for catalysis on the metal surface[8f,g]. Recent develop-ments have been reported on the use of hydrophilic polymeric nanofibres/spheres as supports to immobi-lize nanoparticles[7f ...
Journal of Materials Chemistry, 2011
... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. N... more ... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. Nie, J. Mao, MK Yang, DP Wang, YH Lin, YD Fan, ZL Zhao, H. Wei and XL Ji, Small, 2010, 6, 2558 Article CAS . 30, R. Jin, HF Qian, ZK Wu, Y. Zhu, MZ Zhu, A. Mohanty and N. Garj, J. Phys. ...
Current Organic Synthesis, 2011
Transition-metal-catalyzed coupling of amines with aryl halides (or pseudo-halides) has evolved a... more Transition-metal-catalyzed coupling of amines with aryl halides (or pseudo-halides) has evolved as the most versatile method available to forge carbon-nitrogen bonds. However, due to economic and environmental concerns, the quest for more attractive protocols in both academic and industrial domains has been pursued. In this review, we have summarized recent developments in the use of alternative methodologies, regarding non-conventional reaction medium, activation source and catalyst system, which can be considered promising for C-N cross-coupling reactions (Buchwald-Hartwig, Ullmann and correlates). 142 (96%, 40 min) 143 (85%, 45 min) 144 (79%, 40 min) 145 (86%, 40 min) Scheme 27. Cu-Ni/C catalyzed aryl chloride aminations.
In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal con... more In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal conditions at 55°C with good yields of conversion; better results were obtained with low reaction time. In 1 hour, 1iodo-4-nitrobenzene and phenylboronic acid reached 98% of the yield and 9700 of TON. Better results were obtained with Pd(0) sources. The reaction system was recycled up to three times with good activity.
Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings, 2013
Supramolecular Chemistry, 2006
Cyclodextrins are known by their properties of molecular recognition. In the present work, it was... more Cyclodextrins are known by their properties of molecular recognition. In the present work, it was established, by using high-performance liquid chromatography, that complexes between 2-hydroxypropyl-β-cyclodextrin (HPCD) and d- and l-tryptophan are readily formed in solution. Association constants of (2 ± 1) × 10 and of (9 ± 2) × 10 for d and l-isomers, respectively, were calculated from UV electronic spectroscopy experiments. Solid state complexes were characterized by
The Scientific World Journal, 2013
The formation of Pd(0) in the absence of any classical reducing agent in a medium containing Mg 2... more The formation of Pd(0) in the absence of any classical reducing agent in a medium containing Mg 2+ /Al 3+ layered double hydroxide (LDH) and N,N-dimethylformamide was evidenced. XRD analysis showed the presence of crystalline phases of palladium in the Pd/LDH composite. Suzuki-Miyaura reactions in aqueous medium were carried out at room temperature, and good yields were obtained with bromoarenes and iodoarenes using the ternary system LDH-Pd-CD (cyclodextrin) as catalyst.
ABSTRACT Optimized reaction conditions afford biaryl compounds (III) in high yields.
ChemInform, 2010
Hydroxypropyl-α-cyclodextrin-capped Pd nanoparticles are presented as new efficient catalyst in H... more Hydroxypropyl-α-cyclodextrin-capped Pd nanoparticles are presented as new efficient catalyst in Heck, Sonogashira and Suzuki cross coupling reactions. The reactions can be run in neat water with catalyst loading as low as 0.1-0.05 mol%. The catalyst shows remarkable stability and is easily recovered and reused for at least ten runs. The cyclodextrin serves as a binding site for the substrates and thus, increases the catalytic activity. -(SENRA, J. D.; MALTA*, L. F. B.; DA COSTA, M. E. H. M.; MICHEL, R. C.; AGUIAR, L. C. S.; SIMAS, A. B. C.; ANTUNES, O. A. C.; Adv. Synth. Catal. 351 (2009) 14-15, 2411-2422; Inst. Quim., Univ. Fed. Rio de Janeiro,
Tetrahedron Letters, 2007
... 2(a)AHM de Vries, JMCA Mulders, JHM Mommers, HJW Henderickx and JG de Vries, Org. Lett. (2003... more ... 2(a)AHM de Vries, JMCA Mulders, JHM Mommers, HJW Henderickx and JG de Vries, Org. Lett. (2003). (b)MT Reets and JG de Vries, Chem. Commun. (2004), p. 1559. (c)RK Arvela and NE Leadbeater, J. Org. Chem. 70 (2005), p. 1786. ...
Tetrahedron Letters, 2010
In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal con... more In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal conditions at 55°C with good yields of conversion; better results were obtained with low reaction time. In 1 hour, 1iodo-4-nitrobenzene and phenylboronic acid reached 98% of the yield and 9700 of TON. Better results were obtained with Pd(0) sources. The reaction system was recycled up to three times with good activity.
Letters in Organic Chemistry, 2009
In this report, the recognition points of tryptophan by 2-hydroxypropyl-alpha-cyclodextrin (HP CD... more In this report, the recognition points of tryptophan by 2-hydroxypropyl-alpha-cyclodextrin (HP CD) are presented. This cyclodextrin exhibited greater thermodynamic chiral selectivity towards DL-tryptophan than the hydroxypropylated beta form. FTIR spectroscopy was used to tentatively evidence this chiral discrimination in solid state HP CD-Trp complexes. An inclusion complex was only detected for the HP CD-DTrp sample, while HP CD-LTrp immediately decomposed after crystallization, which left a mechanical mixture of tryptophan and cyclodextrin.
Journal of the Brazilian Chemical Society, 2007
Ligand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain a... more Ligand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain aminoacid racemates. Chiral selector was copper L-phenylalaninate (II) and the results showed the elution of D enantiomer followed by L form. Considering the 3-point interaction concept, a mechanism of chiral recognition was proposed, in which no change of configuration would follow the formation of pseudo-homochiral and heterochiral complexes. To prove the reliability of this mechanism, the trans configuration of homochiral complex had to be more stable than the cis form, which was confirmed by DFT-B3LYP calculation in gas phase. The infrared frequencies were also calculated and the comparison with the subtracted and deconvoluted spectrum of the in-solution complex also pointed to the presence of the trans diasteroisomer.
Journal of Materials Chemistry, 2011
... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. N... more ... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. Nie, J. Mao, MK Yang, DP Wang, YH Lin, YD Fan, ZL Zhao, H. Wei and XL Ji, Small, 2010, 6, 2558 Article CAS . 30, R. Jin, HF Qian, ZK Wu, Y. Zhu, MZ Zhu, A. Mohanty and N. Garj, J. Phys. ...
Current Organic Chemistry, 2010
ABSTRACT Cyclodextrins provide unique opportunities to catalytic applications. The integration of... more ABSTRACT Cyclodextrins provide unique opportunities to catalytic applications. The integration of these supramolecular structures and heterogeneous catalysis exhibits potential to fulfill the high demands to the development of sustainable chemical processes. Herein, we have summarized some properties of this important class of catalysts. Selected synthetic applications are discussed. §We dedicate this manuscript to the memory of Professor Octavio Augusto Ceva Antunes (1952-2009), a leading figure in the catalysis field in Brazil and a masterful teacher and mentor in the chemical sciences. The development of accessible and efficient green catalysts for as many different applications as organic synthesis, biofuels and nutraceutics, was a major theme of his research. His energy and impressive knowledge was always punctuated with humor and wit, the reason why many students, researchers and colleagues were drawn towards him during his life. Octavio Antunes was much more than a scientist. He enjoyed literature, philosophy, languages and culinary and was deeply concerned with his contribution as scientist to social development. He was thus dedicated to increasing the access to antiviral drugs in Brazil. To those who knew him, he was a genuine scientist-humanist. His untimely and tragic loss deeply affected his colleagues and students but the human and scientific legacies he left through an intense and productive life will remain.
Advanced Synthesis & Catalysis, 2009
... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible ... more ... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible sites for catalysis on the metal surface[8f,g]. Recent develop-ments have been reported on the use of hydrophilic polymeric nanofibres/spheres as supports to immobi-lize nanoparticles[7f ...
Advanced Synthesis & Catalysis, 2008
Page 1. DOI: 10.1002/adsc.200800472 Palladium on Calcium Carbonate Combined to 2-Hydroxypropyl-a/... more Page 1. DOI: 10.1002/adsc.200800472 Palladium on Calcium Carbonate Combined to 2-Hydroxypropyl-a/b-cyclodextrins: A Selective Catalytic System for Aqueous Heck Coupling and Hydroarylation Jaqueline D. Senra,a Luiz ...
Advanced Synthesis & Catalysis, 2009
... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible ... more ... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible sites for catalysis on the metal surface[8f,g]. Recent develop-ments have been reported on the use of hydrophilic polymeric nanofibres/spheres as supports to immobi-lize nanoparticles[7f ...
Journal of Materials Chemistry, 2011
... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. N... more ... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. Nie, J. Mao, MK Yang, DP Wang, YH Lin, YD Fan, ZL Zhao, H. Wei and XL Ji, Small, 2010, 6, 2558 Article CAS . 30, R. Jin, HF Qian, ZK Wu, Y. Zhu, MZ Zhu, A. Mohanty and N. Garj, J. Phys. ...
Current Organic Synthesis, 2011
Transition-metal-catalyzed coupling of amines with aryl halides (or pseudo-halides) has evolved a... more Transition-metal-catalyzed coupling of amines with aryl halides (or pseudo-halides) has evolved as the most versatile method available to forge carbon-nitrogen bonds. However, due to economic and environmental concerns, the quest for more attractive protocols in both academic and industrial domains has been pursued. In this review, we have summarized recent developments in the use of alternative methodologies, regarding non-conventional reaction medium, activation source and catalyst system, which can be considered promising for C-N cross-coupling reactions (Buchwald-Hartwig, Ullmann and correlates). 142 (96%, 40 min) 143 (85%, 45 min) 144 (79%, 40 min) 145 (86%, 40 min) Scheme 27. Cu-Ni/C catalyzed aryl chloride aminations.
In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal con... more In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal conditions at 55°C with good yields of conversion; better results were obtained with low reaction time. In 1 hour, 1iodo-4-nitrobenzene and phenylboronic acid reached 98% of the yield and 9700 of TON. Better results were obtained with Pd(0) sources. The reaction system was recycled up to three times with good activity.
Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings, 2013
Supramolecular Chemistry, 2006
Cyclodextrins are known by their properties of molecular recognition. In the present work, it was... more Cyclodextrins are known by their properties of molecular recognition. In the present work, it was established, by using high-performance liquid chromatography, that complexes between 2-hydroxypropyl-β-cyclodextrin (HPCD) and d- and l-tryptophan are readily formed in solution. Association constants of (2 ± 1) × 10 and of (9 ± 2) × 10 for d and l-isomers, respectively, were calculated from UV electronic spectroscopy experiments. Solid state complexes were characterized by
The Scientific World Journal, 2013
The formation of Pd(0) in the absence of any classical reducing agent in a medium containing Mg 2... more The formation of Pd(0) in the absence of any classical reducing agent in a medium containing Mg 2+ /Al 3+ layered double hydroxide (LDH) and N,N-dimethylformamide was evidenced. XRD analysis showed the presence of crystalline phases of palladium in the Pd/LDH composite. Suzuki-Miyaura reactions in aqueous medium were carried out at room temperature, and good yields were obtained with bromoarenes and iodoarenes using the ternary system LDH-Pd-CD (cyclodextrin) as catalyst.
ABSTRACT Optimized reaction conditions afford biaryl compounds (III) in high yields.
ChemInform, 2010
Hydroxypropyl-α-cyclodextrin-capped Pd nanoparticles are presented as new efficient catalyst in H... more Hydroxypropyl-α-cyclodextrin-capped Pd nanoparticles are presented as new efficient catalyst in Heck, Sonogashira and Suzuki cross coupling reactions. The reactions can be run in neat water with catalyst loading as low as 0.1-0.05 mol%. The catalyst shows remarkable stability and is easily recovered and reused for at least ten runs. The cyclodextrin serves as a binding site for the substrates and thus, increases the catalytic activity. -(SENRA, J. D.; MALTA*, L. F. B.; DA COSTA, M. E. H. M.; MICHEL, R. C.; AGUIAR, L. C. S.; SIMAS, A. B. C.; ANTUNES, O. A. C.; Adv. Synth. Catal. 351 (2009) 14-15, 2411-2422; Inst. Quim., Univ. Fed. Rio de Janeiro,
Tetrahedron Letters, 2007
... 2(a)AHM de Vries, JMCA Mulders, JHM Mommers, HJW Henderickx and JG de Vries, Org. Lett. (2003... more ... 2(a)AHM de Vries, JMCA Mulders, JHM Mommers, HJW Henderickx and JG de Vries, Org. Lett. (2003). (b)MT Reets and JG de Vries, Chem. Commun. (2004), p. 1559. (c)RK Arvela and NE Leadbeater, J. Org. Chem. 70 (2005), p. 1786. ...
Tetrahedron Letters, 2010
In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal con... more In this work, we present ligand-free Suzuki cross-coupling reactions in PEG 300 under thermal conditions at 55°C with good yields of conversion; better results were obtained with low reaction time. In 1 hour, 1iodo-4-nitrobenzene and phenylboronic acid reached 98% of the yield and 9700 of TON. Better results were obtained with Pd(0) sources. The reaction system was recycled up to three times with good activity.
Letters in Organic Chemistry, 2009
In this report, the recognition points of tryptophan by 2-hydroxypropyl-alpha-cyclodextrin (HP CD... more In this report, the recognition points of tryptophan by 2-hydroxypropyl-alpha-cyclodextrin (HP CD) are presented. This cyclodextrin exhibited greater thermodynamic chiral selectivity towards DL-tryptophan than the hydroxypropylated beta form. FTIR spectroscopy was used to tentatively evidence this chiral discrimination in solid state HP CD-Trp complexes. An inclusion complex was only detected for the HP CD-DTrp sample, while HP CD-LTrp immediately decomposed after crystallization, which left a mechanical mixture of tryptophan and cyclodextrin.
Journal of the Brazilian Chemical Society, 2007
Ligand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain a... more Ligand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain aminoacid racemates. Chiral selector was copper L-phenylalaninate (II) and the results showed the elution of D enantiomer followed by L form. Considering the 3-point interaction concept, a mechanism of chiral recognition was proposed, in which no change of configuration would follow the formation of pseudo-homochiral and heterochiral complexes. To prove the reliability of this mechanism, the trans configuration of homochiral complex had to be more stable than the cis form, which was confirmed by DFT-B3LYP calculation in gas phase. The infrared frequencies were also calculated and the comparison with the subtracted and deconvoluted spectrum of the in-solution complex also pointed to the presence of the trans diasteroisomer.
Journal of Materials Chemistry, 2011
... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. N... more ... Chem., 2007, 46, 1884 Article CAS . 18, NR Shiju and VV Guliants, Appl. ... 29, N. Zhao, W. Nie, J. Mao, MK Yang, DP Wang, YH Lin, YD Fan, ZL Zhao, H. Wei and XL Ji, Small, 2010, 6, 2558 Article CAS . 30, R. Jin, HF Qian, ZK Wu, Y. Zhu, MZ Zhu, A. Mohanty and N. Garj, J. Phys. ...
Current Organic Chemistry, 2010
ABSTRACT Cyclodextrins provide unique opportunities to catalytic applications. The integration of... more ABSTRACT Cyclodextrins provide unique opportunities to catalytic applications. The integration of these supramolecular structures and heterogeneous catalysis exhibits potential to fulfill the high demands to the development of sustainable chemical processes. Herein, we have summarized some properties of this important class of catalysts. Selected synthetic applications are discussed. §We dedicate this manuscript to the memory of Professor Octavio Augusto Ceva Antunes (1952-2009), a leading figure in the catalysis field in Brazil and a masterful teacher and mentor in the chemical sciences. The development of accessible and efficient green catalysts for as many different applications as organic synthesis, biofuels and nutraceutics, was a major theme of his research. His energy and impressive knowledge was always punctuated with humor and wit, the reason why many students, researchers and colleagues were drawn towards him during his life. Octavio Antunes was much more than a scientist. He enjoyed literature, philosophy, languages and culinary and was deeply concerned with his contribution as scientist to social development. He was thus dedicated to increasing the access to antiviral drugs in Brazil. To those who knew him, he was a genuine scientist-humanist. His untimely and tragic loss deeply affected his colleagues and students but the human and scientific legacies he left through an intense and productive life will remain.
Advanced Synthesis & Catalysis, 2009
... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible ... more ... Octavio Augusto Ceva Antunes. ... hydrophilic thiols which can render partially inaccessible sites for catalysis on the metal surface[8f,g]. Recent develop-ments have been reported on the use of hydrophilic polymeric nanofibres/spheres as supports to immobi-lize nanoparticles[7f ...
Advanced Synthesis & Catalysis, 2008
Page 1. DOI: 10.1002/adsc.200800472 Palladium on Calcium Carbonate Combined to 2-Hydroxypropyl-a/... more Page 1. DOI: 10.1002/adsc.200800472 Palladium on Calcium Carbonate Combined to 2-Hydroxypropyl-a/b-cyclodextrins: A Selective Catalytic System for Aqueous Heck Coupling and Hydroarylation Jaqueline D. Senra,a Luiz ...