Solid-Supported Odorless Reagents for the Dithioacetalization of Aldehydes and Ketones

Jung, Nicole; Gräßle, Simone; Lütjohann, Dominic; Bräse, S.

doi:10.1021/ol403313h

Cited by 29 publications

(14 citation statements)

References 162 publications

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“…The repository is interoperable with the chemotion ELN with respect to data transfer, offers export schemes to other systems and data are curated by automatic checks and a peer reviewing process. The integration of data stored in the repository to publications was shown with several examples (Jung et al 2014, Bär et al 2019, Huang et al 2018). Existing services forming the nucleus of the envisioned federation of repositories as part of the NFDI4Chem infrastructure.…”

Section: Services Provided By the Consortiummentioning

confidence: 99%

NFDI4Chem - Towards a National Research Data Infrastructure for Chemistry in Germany

Steinbeck¹,

Koepler²,

Bach³

et al. 2020

RIO

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The vision of NFDI4Chem is the digitalisation of all key steps in chemical research to support scientists in their efforts to collect, store, process, analyse, disclose and re-use research data. Measures to promote Open Science and Research Data Management (RDM) in agreement with the FAIR data principles are fundamental aims of NFDI4Chem to serve the chemistry community with a holistic concept for access to research data. To this end, the overarching objective is the development and maintenance of a national research data infrastructure for the research domain of chemistry in Germany, and to enable innovative and easy to use services and novel scientific approaches based on re-use of research data. NFDI4Chem intends to represent all disciplines of chemistry in academia. We aim to collaborate closely with thematically related consortia. In the initial phase, NFDI4Chem focuses on data related to molecules and reactions including data for their experimental and theoretical characterisation. This overarching goal is achieved by working towards a number of key objectives: Key Objective 1: Establish a virtual environment of federated repositories for storing, disclosing, searching and re-using research data across distributed data sources. Connect existing data repositories and, based on a requirements analysis, establish domain-specific research data repositories for the national research community, and link them to international repositories. Key Objective 2: Initiate international community processes to establish minimum information (MI) standards for data and machine-readable metadata as well as open data standards in key areas of chemistry. Identify and recommend open data standards in key areas of chemistry, in order to support the FAIR principles for research data. Finally, develop standards, if there is a lack. Key Objective 3: Foster cultural and digital change towards Smart Laboratory Environments by promoting the use of digital tools in all stages of research and promote subsequent Research Data Management (RDM) at all levels of academia, beginning in undergraduate studies curricula. Key Objective 4: Engage with the chemistry community in Germany through a wide range of measures to create awareness for and foster the adoption of FAIR data management. Initiate processes to integrate RDM and data science into curricula. Offer a wide range of training opportunities for researchers. Key Objective 5: Explore synergies with other consortia and promote cross-cutting development within the NFDI. Key Objective 6: Provide a legally reliable framework of policies and guidelines for FAIR and open RDM.

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Section: Services Provided By the Consortiummentioning

confidence: 99%

NFDI4Chem - Towards a National Research Data Infrastructure for Chemistry in Germany

Steinbeck¹,

Koepler²,

Bach³

et al. 2020

RIO

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“…Besides many other well-known transformations of the α-position of ketene 1,3-dithioacetals, the reaction with azo-building blocks has been shown to yield α-azo ketene dithioacetals [23]. This finding was further studied by our group recently in order to show the potential of dithi(ol)anylium salts as an equivalent to ketene dithioacetals [24]. The disadvantages of the current synthetic use of ketene 1,3-dithioacetals are caused by the preparative effort for their isolation (via dithi(ol)anylium species) [25] and their substitution-dependent reactivity which often limits their use to ketenes with electron-withdrawing substituents in α-position [9,26].…”

Section: Introductionmentioning

confidence: 99%

Addition of dithi(ol)anylium tetrafluoroborates to α,β-unsaturated ketones

Huang

Nguyẽ̂n

Gräßle

et al. 2018

Beilstein J. Org. Chem.

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In the presented study, dithi(ol)anylium tetrafluoroborates are added to α,β-unsaturated ketones in a Michael-type reaction yielding diverse substituted ketene diothi(ol)anes. The reactions proceed at room temperature in 1 or 13 h without the need of further additives. The presented procedure is in particular useful for dithi(ol)anylium tetrafluoroborates without electron-withdrawing groups in α-position. This is advantageous with respect to previous approaches, which were limited to the use of ketene dithioacetals substituted with electron-withdrawing groups. Aiming for the systematic investigation of possible steric and electronic influences on the outcome of the reaction, various combinations of electrophiles and nucleophiles were used and the results of the reactions were compared based on the type of the used dithioacetal. The scope of the presented procedure is shown with four additional transformations including the use of additional electrophiles and nucleophiles, the use of a chiral auxiliary and subsequent reduction of selected products. Additionally, we extended the reaction to the synthesis of diene dithiolanes by addition of an ynone to α-alkyl or aryl-substitued dithiolanylium TFBs.

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“…Because of their remarkably applications, a wide range protocols to achieve dithioacetals have been efficiently reported . Among them, these organosulfur compounds have been particularly prepared via thioacetalization of aldehydes though different synthetic methodologies, for instance, using resin‐bounded reagents, solid supported‐linker, in the presence of protic or Lewis acids . However, the vast majority of methodologies reported have used different metals as catalysts, including copper, hafnium, indium, ruthenium, vanadium .…”

Section: Introductionmentioning

confidence: 99%

Sulfamic Acid‐Catalyzed Thioacetalization of Aldehydes under Solvent and Metal‐Free Conditions

et al. 2020

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Herein, we have reported a straightforward methodology for the synthesis of dithioacetals through a metal‐free catalyzed reaction of aldehydes with thiols. In this regard, sulfamic acid proved to be a very efficient catalyst for the preparation of desired products under conventional heating as well as ultrasound irradiation. Generally, the desired products were obtained with reasonable yields through a thioacetalization process, under mild reaction conditions. Noteworthy, sulfamic acid could be recovered from the reaction by simple filtration and it was reused in further reactions and it showed good catalytic activity until the third cycle. In addition, a series of control experiments have also been performed and a plausible reaction mechanism has been illustrated.

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Solid-Supported Odorless Reagents for the Dithioacetalization of Aldehydes and Ketones

Cited by 29 publications

References 162 publications

NFDI4Chem - Towards a National Research Data Infrastructure for Chemistry in Germany

NFDI4Chem - Towards a National Research Data Infrastructure for Chemistry in Germany

Addition of dithi(ol)anylium tetrafluoroborates to α,β-unsaturated ketones

Sulfamic Acid‐Catalyzed Thioacetalization of Aldehydes under Solvent and Metal‐Free Conditions

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