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  • 1.
    Blomkvist, Björn
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Green Chemistry in Chemical Education and Synthetic Applications of Sulfinamides2020Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The preparation of chiral molecules, i.e. compounds that are not identical to their mirror image, is of great interest in the field of organic chemistry. The preparation of a enantiomerically pure molecules is crucial in the development of new pharmaceuticals, agrochemicals and more, since the building blocks of life are chiral and the interactions between enantiomers and receptor are different. Furthermore, an important aspect of chemistry is sustainability, developing new synthetic procedures where green chemistry has been incorporated.

    In chapter 2, the use of Brønsted acid catalysis as well as a combined Brønsted acid and aminocatalytic procedure for the preparation of the chiral synthon tert-butane N-sulfinyl imine. Using HBF4•DEE as a catalyst gave the sulfinylimine in high yields in 2 h. Changing the catalyst to HBF4•DEE and aniline both improved the yields and shortened the reaction time to only 30 min. Furthermore, DFT-calculations were performed for both catalytic systems, providing a proposed mechanism suggesting a six-membered cyclic transition state as the key transition state.

    In chapter 3 a light-assisted method for the preparation of chiral unnatural amino acids is presented. Via a photoredox-catalyzed decarboxylation of carboxylic acids, a carbon radical is generated that adds stereoselectively to an N-sulfinyl imine. This method allows for green synthesis of non-natural amino acids, and compared to previous methods, we have extended the radical source to include carboxylic acids.

    In chapter 4, the use of green chemistry in B.Sc. level teaching is explored through an experimental design project for third-year students, using green chemistry as basis for analysis of literature procedures. Following this, the procedure is implemented in a first-year B.Sc. course. This is proven to be an efficient way to increase the students understanding of organic chemistry, as well as an efficient way to teach green chemistry.

  • 2.
    Blomkvist, Björn
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    HBF4 center dot DEE-catalyzed formation of sulfinyl imines: Synthesis and mechanistic studies2018In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 59, no 13, p. 1249-1253Article in journal (Refereed)
    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. 

  • 3.
    Blomkvist, Björn
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Mild and Rapid Aniline/HBF4 center dot DEE-Catalysed Formation of Sulfinyl Imines2019In: ChemistrySelect, ISSN 2365-6549, Vol. 4, no 25, p. 7431-7436Article in journal (Refereed)
    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.

  • 4.
    Dinér, Peter
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Sadhukhan, Arghya
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Blomkvist, Björn
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Chiral Sulfinamides as Highly Enantioselective Organocatalysts2014In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 6, no 11, p. 3063-3066Article in journal (Refereed)
  • 5.
    Josephson, Philip
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Nykvist, Viktor
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Qasim, Wafa
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Blomkvist, Björn
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Student-Driven Development of Greener Chemistry in Undergraduate Teaching: Synthesis of Lidocaine Revisited2019In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328Article in journal (Refereed)
    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.

    The full text will be freely available from 2020-12-01 09:46
  • 6.
    Shatsky, Andrey
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Blomkvist, Björn
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Liu, Jian-Quan
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Kärkäs, Markus D.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Stereoselective Synthesis of Unnatural α-Amino Acids Through Visible Light-Promoted Decarboxylative C-Radical Addition to a Glyoxylate-Derived Sulfinyl ImineManuscript (preprint) (Other academic)
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