In the wake of the coronavirus disease 2019 (COVID-19) pandemic, staff and students at universities worldwide were forced to swiftly adapt to distance learning in order to continue with tertiary education. One of the main challenges we encountered during this period was a marked disconnect between staff and students, leading to lower motivation and engagement by both parties. To address this issue, we explored the social media platform Instagram as an interactive communication channel to engage first-year pharmacy students during an introductory organic chemistry course. This led to the development of @kemipilot, an open Instagram account where student questions were fielded and answered by creating educational images and videos. Despite being a small-scale study, the overwhelmingly positive student response, as well as comparisons between Instagram and the university student forum, suggest that Instagram may be a useful pedagogical tool to complement existing distance learning platforms, even beyond the COVID-19 pandemic.

Herein, a general, solvent‐free and straightforward thiomethylation of electron deficient heterocycles using BF3·SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3·SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non‐malodorous reagent while the discovery of novel chemical transformations using BF3·SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.

Herein, a method for thioacetalation using BF3SMe2 is presented. The method allows for convenient and odor-free transformation of aldehydes to methyl-dithioacetals, a simple but sparsely reported structural moiety, in good yields with a diverse set of aromatic aldehydes. In addition, a thiomethylative Friedel-Crafts reaction was discovered, affording thiomethylated diarylmethanes in good to excellent yields. The resulting diarylmethane core is of interest as it is found in many biologically active compounds, and its utility is further demonstrated as a novel precursor to unsymmetrical triarylmethanes. This work also highlights the usefulness and the synthetic capabilities of the readily available reagent BF3SMe2 beyond its reactivity profile as a dealkylation reagent.

Diazomethane is a powerful reagent for numerous chemical reactions such as esterifications and the homologation of carboxylic acids. Unfortunately, the synthetic utility of diazomethane is severely limited by its toxicity and highly explosive nature. Diazald® is typically used for ex situ synthesis, however it requires cumbersome and hazardous transfer of diazomethane from a caustic aqueous phase to the reaction medium. Herein, we present a low temperature and base‐free in situ synthesis of diazomethane via a “click and release” reaction between an enamine and sulfonyl azide. Its utility is exemplified by the synthesis of diverse methyl esters in yields of up to 93%. Moreover, diazoketone synthesis from in situ generated diazomethane and acid chlorides was demonstrated for the first time. Finally, trideuteromethylation was achieved using acetone‐d6 as the deuterium source. We anticipate that this method will enable the safer use of diazomethane in organic synthesis and drug discovery programs.