| 1. |
- Doobary, Sayad, 1995-, et al.
(författare)
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Cyclopropenium functionalization
- 2024
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Ingår i: Nature Chemistry. - 1755-4330 .- 1755-4349. ; 16, s. 847-848
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Tidskriftsartikel (refereegranskat)abstract
- Although functionalized cyclopropenes have found uses in many applications, their synthesis has been severely limited. Now, a hypervalent iodine reagent, in conjunction with gold catalysis, has been utilized to control their reactivity, allowing efficient formation of cyclopropenyl alkynes/alkenes.
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| 2. |
- Doobary, Sayad, 1995-, et al.
(författare)
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Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols
- 2024
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Ingår i: Frontiers in Chemistry. - 2296-2646. ; 12
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Tidskriftsartikel (refereegranskat)abstract
- The transition-metal free S-vinylation of thiophenols by vinylbenziodoxolones (VBX) constituted an important step forward in hypervalent iodine-mediated vinylations, highlighting the difference to vinyliodonium salts and that the reaction outcome was influenced by the substitution pattern of the benziodoxolone core. In this study, we report several new classes of hypervalent iodine vinylation reagents; vinylbenziodazolones, vinylbenziodoxolonimine and vinyliodoxathiole dioxides. Their synthesis, structural and electronic properties are described and correlated to the S-vinylation outcome, shedding light on some interesting facets of these reagents.
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| 3. |
- Linde, Erika, 1992-, et al.
(författare)
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Advancements in the Synthesis of Diaryliodonium Salts : Updated Protocols
- 2023
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Ingår i: Advanced Synthesis and Catalysis. - 1615-4150 .- 1615-4169. ; 365:16, s. 2751-2756
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Tidskriftsartikel (refereegranskat)abstract
- Our group has reported several one-pot protocols for the synthesis of diaryliodonium salts, which have been recognized as attractive multi-purpose reagents in areas ranging from organic synthesis to materials chemistry. Over the years, we have identified limitations in the published protocols concerning synthesis of mixed electron-rich and electron-poor, as well as highly electron-poor diaryliodonium salts, as the corresponding starting materials are either too reactive or too unreactive. In this update, we discuss the underlying limitations concerning the stability and reactivity of the involved reagents and provide strategies to overcome these challenges through updated synthetic protocols.
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| 4. |
- Linde, Erika, 1992-, et al.
(författare)
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Synthesis of Complex Diarylamines through a Ring-Opening Difunctionalization Strategy
- 2023
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Ingår i: Angewandte Chemie International Edition. - 1433-7851 .- 1521-3773. ; 62:48
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Tidskriftsartikel (refereegranskat)abstract
- The diarylation and skeletal diversification of unstrained cyclic amines was exploited to expand and modify the favorable properties of this important substrate class with pivotal roles in drug discovery. Cyclic amines were employed in the synthesis of a novel class of amino-substituted diaryliodonium salts, which were converted to highly functionalized diarylamines through an atom-efficient one-pot N-arylation/ring opening reaction with external nucleophiles. The reaction proceeds through in situ formation of a diarylammonium intermediate that undergoes a nucleophilic ring opening by cleavage of the strong C−N bond. A wide variety of diarylamines was obtained through introduction of two different aryl groups of varied electronics, and the retained iodo-substituent enables downfield diversifications of the products. More than 20 nucleophiles, including amines, phenols, carboxylic acids, thiols and halides, were alkylated with high functional group tolerance, and the strategy proved efficient also in in late-stage functionalization of natural products and pharmaceuticals.
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| 5. |
- Olofsson, Berit, 1972-
(författare)
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A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols
- 2002
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Doktorsavhandling (övrigt vetenskapligt/konstnärligt)abstract
- The first part of this thesis describes a synthetic strategythat provides all eight possible isomers of a given vic-aminoalcohol starting from vinylepoxides. The value of a generalroute is evident, as several isomers are needed ininvestigations of structure-activity relationships forpharmacologically active derivatives, and for optimizing theperformance of chiral ligands containing the amino alcoholmoiety.Vinylepoxides, obtained in high enantiomeric excess, werering-opened both with inversion and retention ofstereochemistry, delivering two diastereomeric amino alcoholswith high regio- and stereoselectivity. Via ring-closure toaziridines and subsequent regioselective ring-opening withsuitable oxygen nucleophiles, the two remaining amino alcoholswere selectively achieved.Within this study, two efficient protocols for theregioselective and stereospecific aminolysis of vinylepoxideshave been presented. Comparedto previous methods, theseprocedures use milder reaction conditions, shorter reactiontimes, generally give higher yields and are applicable to alarger set of substrates. Furthermore, the ring-closure ofvic-amino alcohols to the corresponding N-H vinylaziridines hasbeen investigated. Three routes have been found useful, whichone is preferred depends on substrate and scale.In the second part of the thesis, the synthetic strategy isapplied on the synthesis of Sphingosine and its regio- andstereoisomers. Moreover, a rapid way of determining relativeconfiguration of vic-amino alcohols is described, which shouldbe of substantial use when amino alcohols are formed bydiastereoselective reactions.amino alcohols, vinylepoxides, vinylaziridines, oxazolines,oxazolidinones, ring-opening, regioselective,diastereoselective, sphingosine, configuration, NMRspectroscopy.
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