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Publications (10 of 46) Show all publications
Blomkvist, B. & Dinér, P. (2019). Mild and Rapid Aniline/HBF4 center dot DEE-Catalysed Formation of Sulfinyl Imines. ChemistrySelect, 4(25), 7431-7436
Open this publication in new window or tab >>Mild and Rapid Aniline/HBF4 center dot DEE-Catalysed Formation of Sulfinyl Imines
2019 (English)In: ChemistrySelect, ISSN 2365-6549, Vol. 4, no 25, p. 7431-7436Article in journal (Refereed) Published
Abstract [en]

The combination of anline and tetrafluoroboric acid diethyl etherate (2.5 mol% and 5 mol%, respectively) significantly accelerates the formation of sulfinyl imines in dichloromethane and isopropylacetate at room temperature compared to previous procedures. A DFT and NMR spectroscopic study shows that the anilinium tetrafluoroborate complex is solvated by sulfinamide molecules in the initial state and that the rate-limiting step of the reaction is the addition of the sulfinamide molecule to the protonated aniline-based imine. In addition, the catalytic system was also utilised in a one-pot, two step reaction, where the in situ formed sulfinyl imine was arylated in a rhodium catalysed reaction with high diastereoselectivity.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019
Keywords
Sulfinylimines, Organic synthesis, Organocatalysis, DFT, NMR
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-255378 (URN)10.1002/slct.201901218 (DOI)000474296800005 ()2-s2.0-85068481356 (Scopus ID)
Note

QC 20190730

Available from: 2019-07-30 Created: 2019-07-30 Last updated: 2019-07-30Bibliographically approved
Blomkvist, B. & Dinér, P. (2018). HBF4 center dot DEE-catalyzed formation of sulfinyl imines: Synthesis and mechanistic studies. Tetrahedron Letters, 59(13), 1249-1253
Open this publication in new window or tab >>HBF4 center dot DEE-catalyzed formation of sulfinyl imines: Synthesis and mechanistic studies
2018 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 59, no 13, p. 1249-1253Article in journal (Refereed) Published
Abstract [en]

A mild acid-catalysed method is reported for the formation of sulfinyl imines from tert-butanesulfinamide and aromatic or aliphatic aldehydes using tetrafluoroboric acid diethyletherate (10 mol%) in dichloromethane. Reactions were performed at room temperature and gave the corresponding sulfinyl imines in excellent yield after 2 h. A DFT study was performed and a mechanism for the reaction is postulated. 

Place, publisher, year, edition, pages
PERGAMON-ELSEVIER SCIENCE LTD, 2018
Keywords
Sulfinyl imine, Bronsted acid catalysis, Tetrafluoroboric acid, Mechanistic study, DFT
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-225705 (URN)10.1016/j.tetlet.2018.02.051 (DOI)000428007300020 ()2-s2.0-85042402317 (Scopus ID)
Note

QC 20180411, Funding Agency: KTH-Royal Institute of Technology 

Available from: 2018-04-11 Created: 2018-04-11 Last updated: 2018-04-11Bibliographically approved
Timmer, B., Schaufelberger, F., Hammarberg, D., Franzen, J., Ramström, O. & Dinér, P. (2018). Simple and Effective Integration of Green Chemistry and Sustainability Education into an Existing Organic Chemistry Course. Journal of Chemical Education, 95(8), 1301-1306
Open this publication in new window or tab >>Simple and Effective Integration of Green Chemistry and Sustainability Education into an Existing Organic Chemistry Course
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2018 (English)In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 95, no 8, p. 1301-1306Article in journal (Refereed) Published
Abstract [en]

Green chemistry and sustainable development have become increasingly important topics for the education of future chemists. The cross-disciplinary nature of green chemistry and sustainable development often means these subjects are taught in conjunction with other subjects, such as organic chemistry and chemical engineering. Herein, a straightforward and efficient approach for vertical integration of green chemistry concepts within existing undergraduate organic chemistry courses is shown. The gradual self-evaluation, "greenification", and reassessment of an organic chemistry course at KTH Royal Institute of Technology from 2013 to 2017 is described, with particular focus on the laboratory course and a novel green chemistry project designed to promote sustainability thinking and reasoning. The laboratory project, which can also be conducted as an independent organic chemistry laboratory exercise, required students to critically evaluate variations of the same Pechmann condensation experiment according to the twelve principles of green chemistry. The course evaluation shows that, after the modifications, students feel more comfortable with the topics "green chemistry" and "sustainability" and consider these topics more important for their future careers. Furthermore, the ability of students to discuss and critically evaluate green chemistry parameters improved considerably as determined from the laboratory project reports.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2018
Keywords
Second-Year Undergraduate, Organic Chemistry, Problem Solving/Decision Making, Testing/Assessment, Green Chemistry, Reactions
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-240202 (URN)10.1021/acs.jchemed.7b00720 (DOI)000442961800008 ()2-s2.0-85051517648 (Scopus ID)
Note

QC 20181217

Available from: 2018-12-17 Created: 2018-12-17 Last updated: 2018-12-17Bibliographically approved
Wang, L., Duan, L., Ambre, R. B., Quentin, D., Chen, H., Sun, J., . . . Sun, L. (2016). A Nickel (II) PY5 Complex as an Electrocatalyst for Water Oxidation. Journal of Catalysis, 335, 72-78
Open this publication in new window or tab >>A Nickel (II) PY5 Complex as an Electrocatalyst for Water Oxidation
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2016 (English)In: Journal of Catalysis, ISSN 0021-9517, Vol. 335, p. 72-78Article in journal (Refereed) Published
Abstract [en]

A Ni-PY5 [PY5 = 2,6-bis(1,1-bis(2-pyridyl)ethyl)pyridine)] complex has been found to act as an electrocatalyst for oxidizing water to dioxygen in aqueous phosphate buffer solutions. The rate of water oxidation catalyzed by the Ni-PY5 is remarkably enhanced by the proton acceptor base HPO42−, with rate constant of 1820 M−1 s−1. Controlled potential bulk electrolysis with Ni-PY5 at pH 10.8 under an applied potential of 1.5 V vs. normal hydrogen electrode (NHE) resulted in dioxygen formation with a high faradaic efficiency over 90%. A detailed mechanistic study identifies the water nucleophilic attack pathway for water oxidation catalysis.

Place, publisher, year, edition, pages
Elsevier, 2016
Keywords
Nickel complex, Water oxidation catalyst, Electrochemistry, Water nucleophilic attack
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-173670 (URN)10.1016/j.jcat.2015.12.003 (DOI)000371098200007 ()2-s2.0-84954413362 (Scopus ID)
Funder
Swedish Research CouncilKnut and Alice Wallenberg FoundationSwedish Energy Agency
Note

QC 20160208

Available from: 2015-09-16 Created: 2015-09-16 Last updated: 2017-01-25Bibliographically approved
Dinér, P. (2016). Yttrium from Ytterby. Nature Chemistry, 8(2), 192-192
Open this publication in new window or tab >>Yttrium from Ytterby
2016 (English)In: Nature Chemistry, ISSN 1755-4330, E-ISSN 1755-4349, Vol. 8, no 2, p. 192-192Article in journal, Editorial material (Refereed) Published
Place, publisher, year, edition, pages
Nature Publishing Group, 2016
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-181900 (URN)10.1038/nchem.2442 (DOI)000369327200019 ()2-s2.0-84955481775 (Scopus ID)
Note

QC 20160226. QC 20160304

Available from: 2016-02-08 Created: 2016-02-08 Last updated: 2017-11-30Bibliographically approved
Mesas-Sanchez, L. & Dinér, P. (2015). A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst. Chemistry - A European Journal, 21(14), 5623-5631
Open this publication in new window or tab >>A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst
2015 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 14, p. 5623-5631Article in journal (Refereed) Published
Abstract [en]

A detailed computational and kinetic analysis of the acetylation of 1-phenylethanol with acetic anhydride catalyzed by planar chiral 4-(dimethylamino) pyridine (DMAP) catalyst ( )-1 is presented. The study includes a computational investigation of the potential-energy surface including the acylation and stereoselective transition states at the DFT level of theory. Experimentally, the kinetic study shows that the reaction proceeds in a first-order manner in catalyst, whereas both substrates, acetic anhydride and 1-phenylethanol, show fractional order, which is in accordance with steady-state conditions. The fractional order depends on an equilibrium between the free catalyst and the acetylated catalyst.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2015
Keywords
acylation, chirality, density functional calculations, kinetics, nucleophilic addition
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-166343 (URN)10.1002/chem.201405793 (DOI)000352504500041 ()25677932 (PubMedID)2-s2.0-84925127164 (Scopus ID)
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note

QC 20150508 QC 20160113

Available from: 2015-05-08 Created: 2015-05-07 Last updated: 2017-12-04Bibliographically approved
Diaz-Alvarez, A. E., Mesas-Sanchez, L. & Dinér, P. (2014). Access to Optically Pure beta-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst. Molecules, 19(9), 14273-14291
Open this publication in new window or tab >>Access to Optically Pure beta-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst
2014 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 19, no 9, p. 14273-14291Article in journal (Refereed) Published
Abstract [en]

The development of new approaches to obtain optically pure beta-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic beta-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic beta-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

Keywords
non-enzymatic kinetic resolution, beta-hydroxy esters, planar-chiral DMAP catalyst, ferrocenyl catalyst
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-155805 (URN)10.3390/molecules190914273 (DOI)000343093100085 ()2-s2.0-84907092007 (Scopus ID)
Funder
Swedish Research CouncilCarl Tryggers foundation
Note

QC 20141113

Available from: 2014-11-13 Created: 2014-11-13 Last updated: 2017-12-05Bibliographically approved
Dinér, P., Sadhukhan, A. & Blomkvist, B. (2014). Chiral Sulfinamides as Highly Enantioselective Organocatalysts. ChemCatChem, 6(11), 3063-3066
Open this publication in new window or tab >>Chiral Sulfinamides as Highly Enantioselective Organocatalysts
2014 (English)In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 6, no 11, p. 3063-3066Article in journal, Editorial material (Refereed) Published
Keywords
C-C coupling, Lewis acid, Lewis base, organocatalysts, sulfinamides
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-157009 (URN)10.1002/cctc.201402558 (DOI)000344330800004 ()2-s2.0-84915737594 (Scopus ID)
Note

QC 20141205

Available from: 2014-12-05 Created: 2014-12-04 Last updated: 2017-12-05Bibliographically approved
Mesas-Sanchez, L., Diaz-Alvarez, A. E., Koukal, P. & Dinér, P. (2014). Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst. Tetrahedron, 70(24), 3807-3811
Open this publication in new window or tab >>Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst
2014 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, no 24, p. 3807-3811Article in journal (Refereed) Published
Abstract [en]

Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee).

Place, publisher, year, edition, pages
Elsevier, 2014
Keywords
2-Hydroxy-2-arylethylphosphonates, Non-enzymatic kinetic resolution, Planar chiral DMAP derivative catalyst
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-147409 (URN)10.1016/j.tet.2014.03.102 (DOI)000336710200010 ()2-s2.0-84899991575 (Scopus ID)
Funder
Swedish Research Council, 621-2009-4018
Note

QC 20140702

Available from: 2014-07-02 Created: 2014-06-27 Last updated: 2017-12-05Bibliographically approved
Alao, J. P., Michlíková, S., Dinér, P., Grøtli, M. & Sunnerhagen, P. (2014). Selective inhibition of RET mediated cell proliferation in vitro by the kinase inhibitor SPP86. BMC Cancer, 14(853)
Open this publication in new window or tab >>Selective inhibition of RET mediated cell proliferation in vitro by the kinase inhibitor SPP86
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2014 (English)In: BMC Cancer, ISSN 1471-2407, E-ISSN 1471-2407, Vol. 14, no 853Article in journal (Refereed) Published
Abstract [en]

Background

The RET tyrosine kinase receptor has emerged as a target in thyroid and endocrine resistant breast cancer. We previously reported the synthesis of kinase inhibitors with potent activity against RET. Herein, we have further investigated the effect of the lead compound SPP86 on RET mediated signaling and proliferation. Based on these observations, we hypothesized that SPP86 may be useful for studying the cellular activity of RET.

Methods

We compared the effects of SPP86 on RET-induced signaling and proliferation in thyroid cancer cell lines expressing RET-PTC1 (TPC1), or the activating mutations BRAFV600E (8505C) and RASG13R (C643). The effect of SPP86 on RET- induced phosphatidylinositide 3-kinases (PI3K)/Akt and MAPK pathway signaling and cell proliferation in MCF7 breast cancer cells was also investigated.

Results

SPP86 inhibited MAPK signaling and proliferation in RET/PTC1 expressing TPC1 but not 8505C or C643 cells. In TPC1 cells, the inhibition of RET phosphorylation required co-exposure to SPP86 and the focal adhesion kinase (FAK) inhibitor PF573228. In MCF7 cells, SPP86 inhibited RET- induced phosphatidylinositide 3-kinases (PI3K)/Akt and MAPK signaling and estrogen receptorα (ERα) phosphorylation, and inhibited proliferation to a similar degree as tamoxifen. Interestingly, SPP86 and PF573228 inhibited RET/PTC1 and GDNF- RET induced activation of Akt and MAPK signaling to a similar degree.

Conclusion

SPP86 selectively inhibits RET downstream signaling in RET/PTC1 but not BRAFV600E or RASG13R expressing cells, indicating that downstream kinases were not affected. SPP86 also inhibited RET signaling in MCF7 breast cancer cells. Additionally, RET- FAK crosstalk may play a key role in facilitating PTC1/RET and GDNF- RET induced activation of Akt and MAPK signaling in TPC1 and MCF7 cells.

Place, publisher, year, edition, pages
BioMed Central, 2014
Keywords
RET, FAK, Thyroid cancer, Breast cancer, Estrogen receptor, Kinase inhibitor
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-179958 (URN)10.1186/1471-2407-14-853 (DOI)
Note

Qc 20160108

Available from: 2016-01-05 Created: 2016-01-05 Last updated: 2017-12-01Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0001-6782-6622

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