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  1. Book ; Online ; E-Book: Green and sustainable medicinal chemistry

    Summerton, Louise / Sneddon, Helen F. / Jones, Leonie C. / Clark, James H.

    methods, tools and strategies for the 21st century pharmaceutical industry

    (RSC green chemistry ; 46 ; RSC e-book collection)

    2016  

    Institution Royal Society of Chemistry
    Author's details edited by Louise Summerton (University of York, UK), Helen F. Sneddon (GlaxoSmithKline, Stevenage, UK), Leonie C. Jones (University of York, UK), James H. Clark (University of York, UK)
    Series title RSC green chemistry ; 46
    RSC e-book collection
    Collection
    Language English
    Size 1 Online-Ressource (xlix 221 Seiten)
    Publisher Royal Society of Chemistry
    Publishing place Cambridge
    Publishing country Great Britain
    Document type Book ; Online ; E-Book
    Remark Zugriff für angemeldete ZB MED-Nutzerinnen und -Nutzer
    HBZ-ID HT019217135
    ISBN 978-1-78262-594-0 ; 9781782624677 ; 1-78262-594-1 ; 1782624678
    Database ZB MED Catalogue: Medicine, Health, Nutrition, Environment, Agriculture

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  2. Article ; Online: Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

    Jordan, Andrew / Hall, Callum G J / Thorp, Lee R / Sneddon, Helen F

    Chemical reviews

    2022  Volume 122, Issue 6, Page(s) 6749–6794

    Abstract: Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common "go-to" solvents are considered to be "less-preferable" for a number ... ...

    Abstract Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common "go-to" solvents are considered to be "less-preferable" for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and
    MeSH term(s) Chemistry, Organic ; Dimethylformamide ; Solvents/chemistry
    Chemical Substances Solvents ; Dimethylformamide (8696NH0Y2X)
    Language English
    Publishing date 2022-02-24
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Review
    ZDB-ID 207949-5
    ISSN 1520-6890 ; 0009-2665
    ISSN (online) 1520-6890
    ISSN 0009-2665
    DOI 10.1021/acs.chemrev.1c00672
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Experimental and computational insights into the mechanism of the copper(i)-catalysed sulfonylative Suzuki-Miyaura reaction.

    Hall, Callum G J / Sneddon, Helen F / Pogány, Peter / Lindsay, David M / Kerr, William J

    Chemical science

    2023  Volume 14, Issue 24, Page(s) 6738–6755

    Abstract: A mechanistic study into the copper(i)-catalysed sulfonylative Suzuki-Miyaura reaction, incorporating sulfur dioxide, is described. Utilising spectroscopic and computational techniques, an exploration into the individual components of the competing ... ...

    Abstract A mechanistic study into the copper(i)-catalysed sulfonylative Suzuki-Miyaura reaction, incorporating sulfur dioxide, is described. Utilising spectroscopic and computational techniques, an exploration into the individual components of the competing catalytic cycles is delineated, including identification of the resting state catalyst, transmetalation of arylboronic acid onto copper(i), the sulfur dioxide insertion process, and the oxidative addition of aryl halide to Cu
    Language English
    Publishing date 2023-05-31
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/d3sc01337e
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  4. Article: Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

    Jordan, Andrew / Hall, Callum G. J. / Thorp, Lee R. / Sneddon, Helen F.

    Chemical reviews. 2022 Feb. 24, v. 122, no. 6

    2022  

    Abstract: Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number ... ...

    Abstract Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N-methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.
    Keywords carcinogenicity ; dimethylformamide ; flammability ; mutagenicity ; organic chemistry ; solvents
    Language English
    Dates of publication 2022-0224
    Size p. 6749-6794.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 207949-5
    ISSN 1520-6890 ; 0009-2665
    ISSN (online) 1520-6890
    ISSN 0009-2665
    DOI 10.1021/acs.chemrev.1c00672
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  5. Article: Development of a More Sustainable Appel Reaction

    Jordan, Andrew / Denton, Ross M / Sneddon, Helen F

    ACS sustainable chemistry & engineering. 2020 Jan. 14, v. 8, no. 5

    2020  

    Abstract: Herein, we report a green, chromatography-free Appel chlorination and bromination in both catalytic and stoichiometric form. Improved sustainability was achieved via the effective replacement of chlorinated solvents with dimethyl carbonate and the use of ...

    Abstract Herein, we report a green, chromatography-free Appel chlorination and bromination in both catalytic and stoichiometric form. Improved sustainability was achieved via the effective replacement of chlorinated solvents with dimethyl carbonate and the use of triphenylphosphine oxide (PPh3O) as a recyclable organocatalyst. The substrate scope of this halogenated solvent-free reaction was shown to be analogous to a contemporary methodology, and removal and recovery of PPh3O from the desired products were effectively demonstrated. Investigations into the catalytic cycle were conducted, and REACT-IR was demonstrated to be an effective method of reaction monitoring in situ. Optimized methodology was applied to the synthesis of 1-bromo-4-(1-bromoethyl)benzene, a key building block employed during the discovery of a GSK fatty acid synthase inhibitor.
    Keywords aromatic compounds ; bromination ; carbonates ; catalytic activity ; chlorination ; enzyme inhibitors ; fatty-acid synthase ; monitoring ; organocatalysts ; solvents ; stoichiometry
    Language English
    Dates of publication 2020-0114
    Size p. 2300-2309.
    Publishing place American Chemical Society
    Document type Article
    ISSN 2168-0485
    DOI 10.1021/acssuschemeng.9b07069
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  6. Article ; Online: Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry.

    Jordan, Andrew / Stoy, Patrick / Sneddon, Helen F

    Chemical reviews

    2020  Volume 121, Issue 3, Page(s) 1582–1622

    Abstract: Chlorinated solvents were once, and in many places are still, ubiquitous in chemistry laboratories. This review explores the properties that led to such widespread use, why there is now an increasing drive to minimize usage, and what alternatives are ... ...

    Abstract Chlorinated solvents were once, and in many places are still, ubiquitous in chemistry laboratories. This review explores the properties that led to such widespread use, why there is now an increasing drive to minimize usage, and what alternatives are currently available.
    MeSH term(s) Chemistry, Pharmaceutical ; Halogenation ; Hydrocarbons, Chlorinated/chemical synthesis ; Hydrocarbons, Chlorinated/chemistry ; Solvents/chemistry
    Chemical Substances Hydrocarbons, Chlorinated ; Solvents
    Language English
    Publishing date 2020-12-22
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Review
    ZDB-ID 207949-5
    ISSN 1520-6890 ; 0009-2665
    ISSN (online) 1520-6890
    ISSN 0009-2665
    DOI 10.1021/acs.chemrev.0c00709
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

    Jordan, Andrew / Whymark, Kyran D. / Sydenham, Jack / Sneddon, Helen F.

    Green chemistry. 2021 Aug. 31, v. 23, no. 17

    2021  

    Abstract: The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling ... ...

    Abstract The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.
    Keywords carbonates ; esterification ; green chemistry ; methylene chloride ; solvents
    Language English
    Dates of publication 2021-0831
    Size p. 6405-6413.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 2006274-6
    ISSN 1463-9270 ; 1463-9262
    ISSN (online) 1463-9270
    ISSN 1463-9262
    DOI 10.1039/d1gc02251b
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  8. Article: Assessing the Limits of Sustainability for the Delépine Reaction

    Jordan, Andrew / Huang, Shanjun / Sneddon, Helen F / Nortcliffe, Andrew

    ACS sustainable chemistry & engineering. 2020 Aug. 13, v. 8, no. 34

    2020  

    Abstract: Herein, we report our efforts to improve the sustainability of the Delépine reaction for the formation of primary amines from activated alkyl halides. A number of alternative greener, more sustainable solvents to the traditionally employed chloroform ... ...

    Abstract Herein, we report our efforts to improve the sustainability of the Delépine reaction for the formation of primary amines from activated alkyl halides. A number of alternative greener, more sustainable solvents to the traditionally employed chloroform were identified, and the use of dimethyl carbonate (DMC) as a solvent was exemplified in the synthesis of a number of pharmaceutically relevant building blocks including the 40 mmol scale synthesis of N-Boc-3-pyrroline. Green chemistry metrics were calculated to identify areas of the Delépine reaction that could potentially be improved upon. Poor atom economy (A.E.) was identified as a key shortcoming of this methodology, although our efforts to improve A.E. and reduce waste were unfortunately unsuccessful. A preliminary thermal safety evaluation was conducted using differential scanning calorimetry due to stability concerns raised over the nature of the products; none of the products were considered to have shock-sensitive or explosive propagating properties. The limits of potential sustainability improvements that could be achieved are critically discussed including the inherent issues with this methodology such as the release of formaldehyde, generation of carcinogenic bis(chloromethyl)ether, and poor atom economy.
    Keywords carbonates ; carcinogenicity ; chloroform ; differential scanning calorimetry ; formaldehyde ; green chemistry ; primary amines ; solvents ; wastes
    Language English
    Dates of publication 2020-0813
    Size p. 12746-12754.
    Publishing place American Chemical Society
    Document type Article
    ISSN 2168-0485
    DOI 10.1021/acssuschemeng.0c05393
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  9. Article: Synthesis of ¹⁸O-labelled alcohols from unlabelled alcohols

    Beddoe, Rhydian H / Edwards, Daniel C / Goodman, Louis / Sneddon, Helen F / Denton, Ross M

    Chemical communications. 2020 June 16, v. 56, no. 48

    2020  

    Abstract: The synthesis of primary, secondary and tertiary ¹⁸O-enriched alcohols from readily available ¹⁶O-alcohols via a Mitsunobu esterification and hydrolysis is described. The method is further exemplified in the labelling of the active pharmaceutical ... ...

    Abstract The synthesis of primary, secondary and tertiary ¹⁸O-enriched alcohols from readily available ¹⁶O-alcohols via a Mitsunobu esterification and hydrolysis is described. The method is further exemplified in the labelling of the active pharmaceutical ingredient, dropropizine and is shown to be tolerant of modern, separation friendly Mitsunobu reagents.
    Keywords active pharmaceutical ingredients ; alcohols ; esterification ; hydrolysis ; isotope labeling ; stable isotopes
    Language English
    Dates of publication 2020-0616
    Size p. 6480-6483.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d0cc02855j
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  10. Article ; Online: The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art.

    Beddoe, Rhydian H / Sneddon, Helen F / Denton, Ross M

    Organic & biomolecular chemistry

    2018  Volume 16, Issue 42, Page(s) 7774–7781

    Abstract: The Mitsunobu reaction is widely regarded as the pre-eminent method for performing nucleophilic substitutions of alcohols with inversion of configuration. However, its applicability to large-scale synthesis is undermined by the fact that alcohol ... ...

    Abstract The Mitsunobu reaction is widely regarded as the pre-eminent method for performing nucleophilic substitutions of alcohols with inversion of configuration. However, its applicability to large-scale synthesis is undermined by the fact that alcohol activation occurs at the expense of two stoichiometric reagents - a phosphine and an azodicarboxylate. The ideal Mitsunobu reaction would be sub-stoichiometric in the phosphine and azodicarboxylate species and employ innocuous terminal oxidants and reductants to achieve recycling. This Review article provides a summary and analysis of recent advances towards the development of such catalytic Mitsunobu reactions.
    Language English
    Publishing date 2018-10-10
    Publishing country England
    Document type Journal Article ; Review ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/c8ob01929k
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