Case Studies

Synthesis of Functionalized Iodoarenes by Iododecarboxylation of Aromatic Carboxylic Acids

Fateh Veer Singh "Our research group is currently involved in the synthesis of new hypervalent iodine reagents and their applications in organic synthesis. These reagents have received particular attention due to their oxidation properties, mild reaction conditions, and environmentally friendly nature. Generally, hypervalent iodine reagents exist in the form of iodine(III) and iodine(V) reagents. In our on-going research project, we are aiming to synthesize novel iodine(III) reagents 2 by the oxidation of iodoarenes 1 (Scheme 1). In order to synthesize the iodoarenes, Science of Synthesis Online was used as a tool for literature search. Performing a literature search using this tool, we were able to find an excellent method for the synthesis of iodoarenes. "

Fateh Veer Singh, VIT University, Chennai Campus, Chennai, India

Synthetic Approaches to Porphyrins by (2 + 2) Routes

 Zhang Zongyao "In this case study, synthetic approaches toward porphyrins were investigated using Science of Synthesis Online. The search provided us with common synthetic pathways as well as credible remarks. The various bond-forming strategies presented were of great help."

Zhang Zongyao, Renmin University of China, Beijing, China

[ 2 + 2 + 2 ] Cyclotrimerization of Alkynes and Nitriles

Gabriela Siemiaszko "We are interested in [2 + 2 + 2] cyclotrimerizations of alkynes for the preparation of variously substituted benzene rings. Science of Synthesis Online was used to undertake a comprehensive review of this topic."

Gabriela Siemiaszko, Ecole Polytechnique, Palaiseau, France

Analysis of Synthetic Routes toward Allenylsilanes

Valentin Bochatay "In this case study, we investigated possible synthetic approaches toward allenylsilanes (Scheme 1) using Science of Synthesis Online. The survey provided a general and comprehensive picture of the available routes presented in a clear and synthetic way."

Valentin Bochatay, Sorbonne Universités, Paris, France

Palladium-Catalyzed Trimethylenemethane (TMM) Cycloaddition

Chao Zheng "In this case study, a literature survey on palladium-catalyzed trimethylenemethane (TMM) cycloaddition reactions was conducted with Science of Synthesis Online."

Chao Zheng, Shanghai Institute of Organic Chemistry, China 

Cyclopropanation of Unactivated Alkenes

"Science of Synthesis Online is a very useful tool for every synthetic chemist and is complementary to other reaction databases. It also provides a short full text introduction with several relevant examples from the literature for a specific transformation. In some cases an experimental procedure is also included which can be very time-saving."

Aleksandar Stojanovic, Novartis Institutes for Biomedical Research, Basel

Synthesis of α-Oxoaldehyde Hydrates by the Oxidation of Diazo Compounds Using Dimethyldioxirane

"Thieme’s Science of Synthesis Online was used to find possible synthetic routes to α-oxoaldehyde hydrates. The structure-based search was very useful to reach the article we wanted, and the content of the article was informative and concise. Thus, Science of Synthesis Online was found to be an excellent tool to find possible synthetic routes to the compounds of interest."

Akinobu Matsuzawa, Hoshi University, Tokyo

Asymmetric [1,2]-Wittig Rearrangement and Synthesis of Fused Heteroaromatics

"Science of Synthesis Online has been used to identify methods of performing asymmetric [1,2]-Wittig rearrangement reactions. Procedures for the synthesis of benzyl ethers and O-aryl carbamates allowed suitable [1,2]-Wittig rearrangement precursors to be prepared and the chapter on benzo[b]furans provided a comprehensive overview of their Synthesis."

Andrew Harper, University of St Andrews

Analysis of Synthetic Approaches toward Glyoxylic Acids

"In this case study, we investigated possible synthetic approaches toward glyoxylic acids with Science of Synthesis Online. The search was based on Section 20.2.5 (2-Oxo- and 2-Imino-Substituted Alkanoic Acids) and the structure-based query tool. The results of both approaches will be discussed and compared."

Franziska Merkt (left) and Charlotte Gers (right), Heinrich-Heine-Universität, Düsseldorf

Palladium-Catalyzed Cross-Coupling Reactions of Aryl Halides on Sulfur Compounds

"Our research work focuses on the development of a library of novel antibacterial compounds with tetramates as the core scaff old, accessed via a Dieckmann ring closure on a substituted thiazolidine ring. By adding diversity around this tetramate core, we can rapidly generate a library of tetramates which are then assayed for biological potency."

Tharindi Panduwawala, University of Oxford (Moloney Group)

Identification of Synthetic Approaches to Heteroatom-Substituted Phosphine Ligands

"The Science of Synthesis database search has been used to identify possible synthetic approaches to a relatively broad ligand library of phosphine ligands bearing heteroatoms in the carbon backbone. In particular, the structure-based query was found to be a useful tool to quickly identify various synthetic
approaches for the compounds of interest.

Johannes Teichert, TU Berlin

Coupling and Deprotection Methods in Solution-Phase Peptide Synthesis

"The ease of access, intuitive search function and quality of content makes Thieme Chemistry’s Science of Synthesis among the best online research tools out there for synthetic chemists. This case study looks specifically at the use of the Science of Synthesis to locate protocols for the various coupling and deprotection reactions used extensively in solution-phase peptide synthesis."

Stefan Lawrenson, University of York (North Group)

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