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A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related...
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A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related Sulfur Compounds and Their Biological Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2024) | Viewed by 14938

Special Issue Editors

Dr. Florian F. Mulks

E-Mail Website
Guest Editor
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Interests: carbon; lewis acids; lewis bases; dications; dianions; sulfoximines
Renè Hommelsheim

E-Mail Website
Guest Editor Assistant
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Interests: sulfoximines; sulfonimidamides; bioactive compounds; sulfur and heterocyclic chemistry

Special Issue Information

Dear Colleagues,

Prof. Carsten Bolm took up his first faculty position in 1993 at the Philipps-Universität Marburg and moved to the RWTH Aachen University in 1996 where he has remained since. While amassing over 500 publications and 25 awards, he has also served in more than 20 board positions for different journals and led various outreach efforts.

He contributed to broad areas of chemistry with his early works on enantioselective metal catalysis and, later, organocatalysis. His endeavours in this field led to the discovery of the benefits of ballmilling in such reactions over traditional solution chemistry which he has since extended to a manifold of chemical reactions. He further pioneered the chemistry of sulfoximines and related sulfur derivatives, a great number of which are now conveniently available thanks to these efforts and to the growing contributions of the community. In recent years, these compounds have found increasing uses in medicinal chemistry and crop science. This is particularly remarkable as even the parent sulfone functional group is extremely rare in known natural products.

We wish to honour his career and scientific contributions with a Special Issue in Molecules focusing on sulfoximines and related sulfur compounds and their pharmaceutical applications. Please submit your articles, communications, or perspectives that you wish to be included in this Special Issue. Please notify us at your earliest convenience if you wish to contribute to this endeavour.

Dr. Florian F. Mulks
Guest Editor

Renè Hommelsheim
Guest Editor Assistant

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • sulfoximines
  • sulfonimidamides
  • sulfondiimines
  • sulfonamides
  • sulfones
  • organosulfur compounds
  • medicinal chemistry
  • crop protection

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Published Papers (5 papers)

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Research

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14 pages, 1661 KiB  
Article
A General Method to Access Underexplored Ylideneamino Sulfates as Interrupted Beckmann-Type Rearrangement Intermediates
by Yifei Zhou and Alan M. Jones
Molecules 2024, 29(7), 1667; https://doi.org/10.3390/molecules29071667 - 8 Apr 2024
Cited by 1 | Viewed by 997
Abstract
The Beckmann rearrangement of ketoximes to their corresponding amides, using a Brønsted acid-mediated fragmentation and migration sequence, has found wide-spread industrial application. We postulated that the development of a methodology to access ylideneamino sulfates using tributylsulfoammonium betaine (TBSAB) would afford isolable Beckmann-type intermediates [...] Read more.
The Beckmann rearrangement of ketoximes to their corresponding amides, using a Brønsted acid-mediated fragmentation and migration sequence, has found wide-spread industrial application. We postulated that the development of a methodology to access ylideneamino sulfates using tributylsulfoammonium betaine (TBSAB) would afford isolable Beckmann-type intermediates and competent partners for subsequent rearrangement cascades. The ylideneamino sulfates generated, isolated as their tributylammonium salts, are sufficiently activated to undergo Beckmann rearrangement without additional reagent activation. The generation of sulfuric acid in situ from the ylideneamino sulfate giving rise to a routine Beckmann rearrangement and additional amide bond cleavage to the corresponding aniline was detrimental to reaction success. The screening of bases revealed inexpensive sodium bicarbonate to be an effective additive to prevent classic Brønsted acid-mediated fragmentation and achieve optimal conversions of up to 99%. Full article
(This article belongs to the Special Issue A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related Sulfur Compounds and Their Biological Applications)
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12 pages, 1943 KiB  
Article
Rearrangement of Arylsulfamates and Sulfates to Para-Sulfonyl Anilines and Phenols
by Yifei Zhou and Alan M. Jones
Molecules 2024, 29(7), 1445; https://doi.org/10.3390/molecules29071445 - 23 Mar 2024
Cited by 2 | Viewed by 1158
Abstract
The C(sp2)-aryl sulfonate functional group is found in bioactive molecules, but their synthesis can involve extreme temperatures (>190 °C or flash vacuum pyrolysis) and strongly acidic reaction conditions. Inspired by the 1917 Tyrer industrial process for a sulfa dye that [...] Read more.
The C(sp2)-aryl sulfonate functional group is found in bioactive molecules, but their synthesis can involve extreme temperatures (>190 °C or flash vacuum pyrolysis) and strongly acidic reaction conditions. Inspired by the 1917 Tyrer industrial process for a sulfa dye that involved an aniline N(sp2)-SO3 intermediate en route to a C(sp2)-SO3 rearranged product, we investigated tributylsulfoammonium betaine (TBSAB) as a milder N-sulfamation to C-sulfonate relay reagent. Initial investigations of a stepwise route involving TBSAB on selected anilines at room temperature enabled the isolation of N(sp2)-sulfamate. Subsequent thermal rearrangement demonstrated the intermediary of a sulfamate en route to the sulfonate; however, it was low-yielding. Investigation of the N-sulfamate to C--sulfonate mechanism through control experiments with variation at the heteroatom positions and kinetic isotope experiments (KIEH/D) confirmed the formation of a key N(sp2)-SO3 intermediate and further confirmed an intermolecular mechanism. Furthermore, compounds without an accessible nitrogen (or oxygen) lone pair did not undergo sulfamation- (or sulfation) -to-sulfonation under these conditions. A one-pot sulfamation and thermal sulfonation reaction was ultimately developed and explored on a range of aniline and heterocyclic scaffolds with high conversions, including N(sp2)-sulfamates (O(sp2)-sulfates) and C(sp2)-sulfonates, in up to 99 and 80% (and 88% for a phenolic example) isolated yield, respectively. Encouragingly, the ability to modulate the ortho-para selectivity of the products obtained was observed under thermal control. A sulfonated analog of the intravenous anesthetic propofol was isolated (88% yield), demonstrating a proof-of-concept modification of a licensed drug alongside a range of nitrogen- and sulfur-containing heterocyclic fragments used in drug discovery. Full article
(This article belongs to the Special Issue A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related Sulfur Compounds and Their Biological Applications)
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17 pages, 1581 KiB  
Article
Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines
by Koneti Kondalarao, Somratan Sau and Akhila K. Sahoo
Molecules 2023, 28(13), 5014; https://doi.org/10.3390/molecules28135014 - 27 Jun 2023
Cited by 3 | Viewed by 1592
Abstract
In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation of S–aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this [...] Read more.
In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation of S–aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this redox-neutral process is the utilization of vinylene carbonate as an oxidizing acetylene surrogate and an efficient vinylene transfer agent. This vinylene carbonate enables the cyclization with the sulfoximine motifs, successfully forming a diverse array of 1,2-benzothiazine derivatives in moderate to good yields. Importantly, this study highlights the potential of Rh(III)-catalyzed C–H activation and [4+2]-annulation reactions for the synthesis of optically pure 1,2-benzothiazines with high enantiomeric purity. Full article
(This article belongs to the Special Issue A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related Sulfur Compounds and Their Biological Applications)
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Review

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23 pages, 8705 KiB  
Review
Recent Advances in the Synthesis of Cyclic Sulfoximines via C–H Bond Activation
by Bingren Wang, Xiayu Liang and Qingle Zeng
Molecules 2023, 28(3), 1367; https://doi.org/10.3390/molecules28031367 - 1 Feb 2023
Cited by 11 | Viewed by 2901
Abstract
Sulfoximines, a ubiquitous class of structural motifs, are widely present in bioactive molecules and functional materials that have received considerable attention from modern organic chemistry, pharmaceutical industries, and materials science. Sulfoximines have proved to be an effective directing group for C–H functionalization which [...] Read more.
Sulfoximines, a ubiquitous class of structural motifs, are widely present in bioactive molecules and functional materials that have received considerable attention from modern organic chemistry, pharmaceutical industries, and materials science. Sulfoximines have proved to be an effective directing group for C–H functionalization which was widely investigated for the synthesis of cyclic sulfoximines. Within the last decade, great progress has been achieved in the synthesis of cyclic sulfoximines. Thus, this review highlights the recent advances in the synthesis of cyclic sulfoximines via the C–H activation strategy and is classified based on the substrate types. Full article
(This article belongs to the Special Issue A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related Sulfur Compounds and Their Biological Applications)
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15 pages, 3895 KiB  
Review
Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer
by Renzo Luisi and James A. Bull
Molecules 2023, 28(3), 1120; https://doi.org/10.3390/molecules28031120 - 22 Jan 2023
Cited by 17 | Viewed by 7354
Abstract
The development of NH transfer reactions using hypervalent iodine and simple sources of ammonia has facilitated the synthesis of sulfoximines and sulfonimidamides for applications across the chemical sciences. Perhaps most notably, the methods have been widely applied in medicinal chemistry and in the [...] Read more.
The development of NH transfer reactions using hypervalent iodine and simple sources of ammonia has facilitated the synthesis of sulfoximines and sulfonimidamides for applications across the chemical sciences. Perhaps most notably, the methods have been widely applied in medicinal chemistry and in the preparation of biologically active compounds, including in the large-scale preparation of an API intermediate. This review provides an overview of the development of these synthetic methods involving an intermediate iodonitrene since our initial report in 2016 on the conversion of sulfoxides into sulfoximines. This review covers the NH transfer to sulfoxides and sulfinamides, and the simultaneous NH/O transfer to sulfides and sulfenamides to form sulfoximines and sulfonimidamides, respectively. The mechanism of the reactions and the identification of key intermediates are discussed. Developments in the choice of reagents, and in the reaction conditions and setups used are described. Full article
(This article belongs to the Special Issue A Themed Issue Dedicated to Professor Carsten Bolm—Sulfoximines and Related Sulfur Compounds and Their Biological Applications)
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