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Publications (10 of 53) Show all publications
Izquierdo, J., Demurget, N., Landa, A., Brinck, T., Mercero, J. M., Dinér, P., . . . Palomo, C. (2019). Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes. Chemistry - A European Journal
Open this publication in new window or tab >>Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes
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2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765Article in journal (Refereed) Published
Abstract [en]

A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface (B3LYP/6-31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH, 2019
Keywords
asymmetric catalysis, azaarenes, Bronsted bases, hydantoins, quaternary stereocenters
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-261019 (URN)10.1002/chem.201902817 (DOI)000484834700001 ()31318987 (PubMedID)2-s2.0-85072225163 (Scopus ID)
Note

QC 20191010

Available from: 2019-10-10 Created: 2019-10-10 Last updated: 2019-10-10Bibliographically approved
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: 2019-12-04Bibliographically approved
Blomkvist, B. & Dinér, P. (2019). Mild and Rapid Aniline/HBF4•DEE‐Catalysed Formation of Sulfinyl Imines. ChemistrySelect
Open this publication in new window or tab >>Mild and Rapid Aniline/HBF4•DEE‐Catalysed Formation of Sulfinyl Imines
2019 (English)In: ChemistrySelectArticle 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.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-264506 (URN)10.1002/slct.201901218 (DOI)000474296800005 ()2-s2.0-85068481356 (Scopus ID)
Note

QC 20191202

Available from: 2019-11-28 Created: 2019-11-28 Last updated: 2019-12-02Bibliographically approved
Blomkvist, B., Dinér, P., Josephson, P., Qasim, W. & Nykvist, V. (2019). Student-Driven Development of Greener Chemistry in Undergraduate Teaching: Synthesis of Lidocaine Revisited. Journal of Chemical Education, 1389-1394
Open this publication in new window or tab >>Student-Driven Development of Greener Chemistry in Undergraduate Teaching: Synthesis of Lidocaine Revisited
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2019 (English)In: Journal of Chemical Education, p. 1389-1394Article in journal (Refereed) Published
Abstract [en]

Green chemistry and sustainable development have become increasingly important topics for the education of future chemists, but the implementation of green chemistry into the chemistry curriculum requires significant efforts from teachers, especially in laboratory education. A student-driven development of a greener synthesis of Lidocaine was performed by three first-cycle, third-year students as a part of their B. Sc. degree project with the goal to implement the procedure in an under-graduate organic chemistry course. The students were merely provided with the framework for the project and were given the opportunity to independently develop the project based on an analysis of the 12 principles of green chemistry. The "greenification" of the Lidocaine synthesis by the three students led to several green improvements of the standard procedure, for example, (1) decreased reaction temperature, (2) solvent replacement, (3) fewer equivalents of the starting material (diethylamine) by the use of an inorganic bulk base, (4) use of catalytic amounts of potassium iodide to promote the Finkelstein reaction, and (5) a two-step one-pot procedure. Furthermore, one of the developed procedures was successfully implemented in a full-scale organic chemistry laboratory course.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019
National Category
Organic Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-264402 (URN)10.1021/acs.jchemed.8b00567 (DOI)2-s2.0-85066912738 (Scopus ID)
Note

QC 20191202

Available from: 2019-11-28 Created: 2019-11-28 Last updated: 2019-12-02Bibliographically approved
Josephson, P., Nykvist, V., Qasim, W., Blomkvist, B. & Dinér, P. (2019). Student-Driven Development of Greener Chemistry in Undergraduate Teaching: Synthesis of Lidocaine Revisited. Journal of Chemical Education
Open this publication in new window or tab >>Student-Driven Development of Greener Chemistry in Undergraduate Teaching: Synthesis of Lidocaine Revisited
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2019 (English)In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328Article in journal (Refereed) Published
Abstract [en]

Green chemistry and sustainable development have become increasingly important topics for the education of future chemists, but the implementation of green chemistry into the chemistry curriculum requires significant efforts from teachers, especially in laboratory education. A student-driven development of a greener synthesis of Lidocaine was performed by three first-cycle, third-year students as a part of their B. Sc. degree project with the goal to implement the procedure in an under-graduate organic chemistry course. The students were merely provided with the framework for the project and were given the opportunity to independently develop the project based on an analysis of the 12 principles of green chemistry. The "greenification" of the Lidocaine synthesis by the three students led to several green improvements of the standard procedure, for example, (1) decreased reaction temperature, (2) solvent replacement, (3) fewer equivalents of the starting material (diethylamine) by the use of an inorganic bulk base, (4) use of catalytic amounts of potassium iodide to promote the Finkelstein reaction, and (5) a two-step one-pot procedure. Furthermore, one of the developed procedures was successfully implemented in a full-scale organic chemistry laboratory course.

National Category
Organic Chemistry Educational Sciences
Identifiers
urn:nbn:se:kth:diva-264909 (URN)2-s2.0-85066912738 (Scopus ID)
Note

QC 20191209

Available from: 2019-12-04 Created: 2019-12-04 Last updated: 2019-12-09Bibliographically 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: 2019-12-04Bibliographically approved
Blomkvist, B. & Dinér, P. (2018). HBF4·DEE-catalyzed formation of sulfinyl imines: Synthesis and mechanistic studies. Tetrahedron Letters, 59, 1249-1253
Open this publication in new window or tab >>HBF4·DEE-catalyzed formation of sulfinyl imines: Synthesis and mechanistic studies
2018 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 59, p. 1249-1253Article in journal (Refereed) Published
Place, publisher, year, edition, pages
Elsevier, 2018
National Category
Organic Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-264505 (URN)10.1016/j.tetlet.2018.02.051 (DOI)000428007300020 ()2-s2.0-85042402317 (Scopus ID)
Note

QC 20191202

Available from: 2019-11-28 Created: 2019-11-28 Last updated: 2019-12-02Bibliographically 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
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0001-6782-6622

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