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Nilsson, Peter
Publications (10 of 24) Show all publications
Sävmarker, J., Lindh, J., Nilsson, P., Sjöberg, P. & Larhed, M. (2012). Oxidative Heck Reactions Using Aryltrifluoroborates and Aryl N-Methyliminodiacetic Acid (MIDA) Boronates. ChemistryOpen, 1(3), 140-146
Open this publication in new window or tab >>Oxidative Heck Reactions Using Aryltrifluoroborates and Aryl N-Methyliminodiacetic Acid (MIDA) Boronates
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2012 (English)In: ChemistryOpen, ISSN 2191-1363, Vol. 1, no 3, p. 140-146Article in journal (Refereed) Published
Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlagsgesellschaft, 2012
Keywords
Heck reactions, N-methyliminodiacetic acid (MIDA), oxidative reactions, palladium complexes, trifluoroborate
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-167718 (URN)10.1002/open.201200007 (DOI)000328607400004 ()
Funder
Swedish Research Council
Available from: 2012-01-31 Created: 2012-01-31 Last updated: 2017-12-08Bibliographically approved
Nilsson, P., Olofsson, K. & Larhed, M. (2009). Focus on Regioselectivity and Product Outcome in Organic Synthesis. In: Martin Oestreich (Ed.), The Mizoroki-Heck Reaction: (pp. 133-162). Hoboken, NJ: John Wiley & Sons
Open this publication in new window or tab >>Focus on Regioselectivity and Product Outcome in Organic Synthesis
2009 (English)In: The Mizoroki-Heck Reaction / [ed] Martin Oestreich, Hoboken, NJ: John Wiley & Sons, 2009, p. 133-162Chapter in book (Other academic)
Place, publisher, year, edition, pages
Hoboken, NJ: John Wiley & Sons, 2009
National Category
Medical and Health Sciences
Identifiers
urn:nbn:se:uu:diva-141859 (URN)10.1002/9780470716076.ch3 (DOI)9780470716076 (ISBN)047071607X (ISBN)9786612022425 (ISBN)6612022426 (ISBN)
Available from: 2011-01-12 Created: 2011-01-12 Last updated: 2013-07-04Bibliographically approved
Lindh, J., Sävmarker, J., Nilsson, P., Sjöberg, P. J. & Larhed, M. (2009). Synthesis of styrenes by palladium(II)-catalyzed vinylation of arylboronic acids and aryltrifluoroborates by using vinyl acetate. Chemistry - A European Journal, 15(18), 4630-4636
Open this publication in new window or tab >>Synthesis of styrenes by palladium(II)-catalyzed vinylation of arylboronic acids and aryltrifluoroborates by using vinyl acetate
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2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 18, p. 4630-4636Article in journal (Refereed) Published
Abstract [en]

Reactions of aromatic and heteroaromatic boronic acids or aryltrifluoroborate salts with vinyl acetate in the presence of a palladium(II) catalyst give the corresponding styrenes in good yields. This Heck reaction proceeds with microwave heating in less than 30 min at 140 degrees C in the absence of base and tolerates a variety of substituents. No palladium reoxidant is needed and the vinylation is performed under non-inert conditions. Mass spectrometry (electrospray ionization mass spectrometry (ESIMS) and tandem mass spectrometry   (MS/MS)) was used to identify cationic palladium-containing complexes in ongoing reactions. The key intermediates that have been detected, together with experiments that used deuterated vinyl acetate, support the existence of catalytically active palladium hydride species, and that it is the arylation of ethylene, not vinyl acetate, which   generates the styrene product. The mechanism of the reaction is discussed in terms of the palladium(II) intermediates mentioned above.

Keywords
Heck reaction, mass spectrometry, mechanistic studies, palladium, styrene
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-102918 (URN)10.1002/chem.200802744 (DOI)000265955200018 ()19274694 (PubMedID)
Available from: 2009-05-13 Created: 2009-05-12 Last updated: 2017-12-13Bibliographically approved
Svennebring, A., Sjöberg, P., Larhed, M. & Nilsson, P. (2008). A mechanistic study on modern palladium catalyst precursors as new gateways to Pd(0) in cationic Heck reactions. Tetrahedron, 64(8), 1808-1812
Open this publication in new window or tab >>A mechanistic study on modern palladium catalyst precursors as new gateways to Pd(0) in cationic Heck reactions
2008 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 64, no 8, p. 1808-1812Article in journal (Refereed) Published
Abstract [en]

Electrospray ionization mass spectrometry (ESI-MS) was used as a means to directly identify catalytic cationic organopalladium species in ligand-controlled Heck reactions involving electron-rich olefins and different Pd-sources. In these high-temperature Heck arylations, the oxidative addition intermediates were observed as bidentate ligand chelated cationic aryl palladium species, suggesting that the used ligand attaches to the metal center at the very beginning of the catalytic cycle. This was also in agreement with the obtained regioisomeric profile of the isolated products. The investigation supports the standard Pd(0)/Pd(II) Heck mechanism and provides further insight regarding the conceivable composition of fundamental Pd(II) intermediates in an ongoing Heck reaction.

Keywords
ESI-MS, Heck, palladium, microwave
National Category
Pharmaceutical Sciences
Identifiers
urn:nbn:se:uu:diva-95221 (URN)10.1016/j.tet.2007.11.111 (DOI)000253620600028 ()
Available from: 2006-11-23 Created: 2006-11-23 Last updated: 2018-01-13Bibliographically approved
Datta, G. K., Nordeman, P., Dackenberg, J., Nilsson, P., Hallberg, A. & Larhed, M. (2008). Enantiopure 2-Aryl-2-Methyl Cyclopentanones by an Asymmetric Chelation-Controlled Heck Reaction Using Aryl Bromides: Increased Preparative Scope and Effect of Ring Size on Reactivity and Selectivity. Tetrahedron: asymmetry, 19(9), 1120-1126
Open this publication in new window or tab >>Enantiopure 2-Aryl-2-Methyl Cyclopentanones by an Asymmetric Chelation-Controlled Heck Reaction Using Aryl Bromides: Increased Preparative Scope and Effect of Ring Size on Reactivity and Selectivity
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2008 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 19, no 9, p. 1120-1126Article in journal (Refereed) Published
Abstract [en]

Quaternary 2-aryl-2-methyl cyclopentanones were obtained in 85–94% ee via Pd(0)-catalyzed chelation-controlled asymmetric arylation of a cyclopentenyl ether with aryl bromides and subsequent hydrolysis. Two new cyclohexenyl ethers were synthesized and evaluated as Heck substrates with both aryl iodides and bromides under different reaction conditions. Arylations of the six-membered vinyl ether 1-methyl-2-(S)-(cyclohex-1-enyloxymethyl)-pyrrolidine with aryl bromides were achieved with t-Bu3P-promoted palladium catalysis using either classical or microwave heating. Isolated Heck products were also obtained in high diastereoselectivities (94–98% de).

National Category
Pharmaceutical Sciences
Identifiers
urn:nbn:se:uu:diva-97435 (URN)10.1016/j.tetasy.2008.04.004 (DOI)000256935800012 ()
Available from: 2008-08-27 Created: 2008-08-27 Last updated: 2018-01-13Bibliographically approved
Nilsson, P. & Hansson, P. (2007). Deswelling Kinetics of Polyacrylate Gels in Solutions of Cetyltrimethylammonium Bromide. Journal of Physical Chemistry B, 111(33), 9770-9778
Open this publication in new window or tab >>Deswelling Kinetics of Polyacrylate Gels in Solutions of Cetyltrimethylammonium Bromide
2007 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 111, no 33, p. 9770-9778Article in journal (Refereed) Published
Abstract [en]

The deswelling kinetics of single sodium polyacrylate gel beads (radius 40−160 μm) in aqueous solutions of cetyltrimethylammonium bromide under conditions of forced convection are investigated using micromanipulator assisted light microscopy. The purpose of the study is to further evaluate a previously published model (J. Phys. Chem. B 2003, 107, 9203) using a higher homolog surfactant. For gels with expected fast deswelling (small gel size/low surfactant concentration) and/or in low electrolyte concentration, the model is found to correctly predict the deswelling characteristics of the gel beads. However, for some gels with expected slow deswelling, especially in high electrolyte concentration (10 mM NaBr), the model widely underestimates the required deswelling time. The reason for this is argued to be the longer time frame and high bromide concentration allowing the formation of a denser, more ordered structure in the surface phase, which resists the deformation and reorganization of material necessary for deswelling. Unexpectedly long lag times before the start of deswelling are also found for gels in low surfactant concentration, indicating that a relatively high surfactant concentration in the gel, greatly exceeding the critical aggregation concentration, is needed to start formation of a collapsed surface phase. This critical surfactant concentration is found to be dependent on initial gel radius, as small gels require a relatively higher concentration to initiate collapse.

National Category
Pharmaceutical Sciences
Identifiers
urn:nbn:se:uu:diva-96225 (URN)10.1021/jp0728151 (DOI)000248759000012 ()17655349 (PubMedID)
Available from: 2007-09-27 Created: 2007-09-27 Last updated: 2018-06-04Bibliographically approved
Nilsson, P., Unga, J. & Hansson, P. (2007). Effect of Salt and Surfactant Concentration on the Structure of Polyacrylate Gel/Surfactant Complexes. Journal of Physical Chemistry B, 111(37), 10959-10964
Open this publication in new window or tab >>Effect of Salt and Surfactant Concentration on the Structure of Polyacrylate Gel/Surfactant Complexes
2007 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 111, no 37, p. 10959-10964Article in journal (Refereed) Published
Abstract [en]

Small-angle X-ray scattering was used to elucidate the structure of crosslinked polyacrylate gel/dodecyltrimethylammonium bromide complexes equilibrated in solutions of varying concentrations of surfactant and sodium bromide (NaBr). Samples were swollen with no ordering (micelle free), or they were collapsed with either several distinct peaks (cubic Pm3n) or one broad correlation peak (disordered micellar). The main factor determining the structure of the collapsed complexes was found to be the NaBr concentration, with the cubic structure existing up to 150 mM NaBr and above which only the disordered micellar structure was found. Increasing the salt concentration decreases the polyion mediated attractive forces holding the micelles together causing swelling of the gel. At sufficiently high salt concentration the micelle−micelle distance in the gel becomes too large for the cubic structure to be retained, and it melts into a disordered micellar structure. As most samples were above the critical micelle concentration, the bulk of the surfactant was in the form of micelles in the solution and the surfactant concentration thereby had only a minor influence on the structure. However, in the region around 150 mM NaBr, increasing the surfactant concentration, at constant NaBr concentration, was found to change the structure from disordered micellar to ordered cubic and back to disordered again.

National Category
Pharmaceutical Sciences Natural Sciences
Identifiers
urn:nbn:se:uu:diva-96226 (URN)10.1021/jp074112p (DOI)000249501700016 ()17715959 (PubMedID)
Available from: 2007-09-27 Created: 2007-09-27 Last updated: 2018-06-04Bibliographically approved
Olofsson, K., Nilsson, P. & Larhed, M. (2006). Accelerated Chemistry: Microwave, Sonochemical, and Fluorous Phase Techniques. In: Bartlett, Paul Allan & Entzeroth, M (Ed.), Exploiting chemical diversity for drug discovery: (pp. 33-48). Royal Chemical Society
Open this publication in new window or tab >>Accelerated Chemistry: Microwave, Sonochemical, and Fluorous Phase Techniques
2006 (English)In: Exploiting chemical diversity for drug discovery / [ed] Bartlett, Paul Allan & Entzeroth, M, Royal Chemical Society , 2006, p. 33-48Chapter in book (Other academic)
Place, publisher, year, edition, pages
Royal Chemical Society, 2006
National Category
Medical and Health Sciences
Identifiers
urn:nbn:se:uu:diva-75632 (URN)10.1039/9781847552556-00137 (DOI)9780854048427 (ISBN)
Available from: 2006-02-13 Created: 2006-02-13 Last updated: 2013-11-13Bibliographically approved
Enquist, P.-A., Nilsson, P., Sjöberg, P. & Larhed, M. (2006). ESI-MS Detection of Proposed Reaction Intermediates in the Air-Promoted and Ligand-Modulated Oxidative Heck Reaction. Journal of Organic Chemistry, 71(23), 8779-8786
Open this publication in new window or tab >>ESI-MS Detection of Proposed Reaction Intermediates in the Air-Promoted and Ligand-Modulated Oxidative Heck Reaction
2006 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, no 23, p. 8779-8786Article in journal (Refereed) Published
Abstract [en]

Electrospray ionization mass spectrometry (ESI-MS) and subsequent MS/MS analyses were used to directly detect palladium-containing cationic reaction intermediates in a ligand controlled palladium(II)-catalyzed oxidative Heck arylation. All potential intermediates were observed as dmphen-ligated palladium(II) species, suggesting that the dmphen bidentate ligand is attached to the metal center during the entire catalytic cycle. The study supports previous mechanistic propositions and provides new information regarding the composition of aryl-containing Pd(II) complexes in an ongoing oxidative Heck reaction. In addition, sodium acetate was found to be a useful base alternative to previously used tertiary amines.

National Category
Pharmaceutical Sciences
Identifiers
urn:nbn:se:uu:diva-94793 (URN)10.1021/jo061437d (DOI)000241755300013 ()17081006 (PubMedID)
Available from: 2006-09-14 Created: 2006-09-14 Last updated: 2018-06-04Bibliographically approved
Nilsson, P., Olofsson, K. & Larhed, M. (2006). Microwave-assisted and metal-catalyzed coupling reactions. Top. Curr. Chem. (266), 103-144
Open this publication in new window or tab >>Microwave-assisted and metal-catalyzed coupling reactions
2006 (English)In: Top. Curr. Chem., no 266, p. 103-144Article in journal (Refereed) Published
Identifiers
urn:nbn:se:uu:diva-24812 (URN)
Available from: 2007-02-07 Created: 2007-02-07 Last updated: 2011-01-11
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