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Two graduate-level courses were designed to advance creative, interdisciplinary teamwork among graduate students. Over three years, the two courses underwent three iterations largely focused on refinements to teamwork, which led to high-quality student products. This design case presents the three course iterations, how course design decisions were made, and the kind of results that were achieved. The paper concludes with reflections for designing higher education courses focused on creativity, interdisciplinarity, and teamwork.

 

A dearomatization-dislocation-coupling cascade rapidly transforms aromatic isocyanides into highly functionalized cyclohexadienes. The facile cascade installs an exceptional degree of molecular complexity: three carbon-carbon bonds, two quaternary stereocenters, and three orthogonal functionalities, a cyclohexadiene, a nitrile, and an isocyanide. The tolerance of arylisocyanides makes the method among the mildest dearomatizations ever reported, typically occurring within minutes at −78 °C. Experimental and computational analyses implicate an electron transfer-initiated mechanism involving an unprecedented isocyanide rearrangement followed by radical-radical anion coupling. The dearomatization is fast, proceeds via a complex cascade mechanism supported by experimental and computational insight, and provides complex, synthetically valuable cyclohexadienes.

 

Scientific research is an open‐ended quest where success usually triumphs over failure. The tremendous success of science obscures the tendency for the non‐linear discovery process to take longer and cost more than expected. Perseverance through detours and past setbacks requires a significant commitment that is fueled by scientific optimism; the same optimism required to overcome challenges simultaneously exacerbates the very human tendency to continue a line of inquiry when the likelihood of success is minimal, the so‐called sunk‐cost bias. This Viewpoint Article shows how the psychological phenomenon of sunk‐cost bias influences medicinal, pharmaceutical, and organic chemists by comparing how the respective industrial and academic practitioners approach sunk‐cost bias; a series of interviews and illustrative quotes provide a rich trove of data to address this seldom discussed, yet potentially avoidable research cost. The concluding strategies recommended for mitigating against sunk‐cost bias should benefit not only medicinal, pharmaceutical, and organic chemists but a wide array of chemistry practitioners.

 

Scientific research is an open‐ended quest where success usually triumphs over failure. The tremendous success of science obscures the tendency for the non‐linear discovery process to take longer and cost more than expected. Perseverance through detours and past setbacks requires a significant commitment that is fueled by scientific optimism; the same optimism required to overcome challenges simultaneously exacerbates the very human tendency to continue a line of inquiry when the likelihood of success is minimal, the so‐called sunk‐cost bias. This Viewpoint Article shows how the psychological phenomenon of sunk‐cost bias influences medicinal, pharmaceutical, and organic chemists by comparing how the respective industrial and academic practitioners approach sunk‐cost bias; a series of interviews and illustrative quotes provide a rich trove of data to address this seldom discussed, yet potentially avoidable research cost. The concluding strategies recommended for mitigating against sunk‐cost bias should benefit not only medicinal, pharmaceutical, and organic chemists but a wide array of chemistry practitioners.

 

Metalated isocyanides are highly versatile organometallics. Central to the reactivity of metalated isocyanides is the presence of two orthogonally reactive carbons, a highly nucleophilic “carbanion” inductively stabilized by a carbene-like isocyanide carbon. The two reactivities are harnessed in the attack of metalated isocyanides on π-electrophiles where an initial nucleophilic attack leads to an electron pair that cyclizes onto the terminal isocyanide carbon in a rapid route to diverse, nitrogenous heterocycles. Harnessing the potent nucleophilicity of metalated isocyanides while preventing electrophilic attack on the terminal isocyanide carbon has largely been driven by empirical heuristics. This review provides a foundational understanding by surveying the formation, structure, and properties of metalated isocyanides. The focus on the interplay between the structure and reactivity of metalated isocyanides is anticipated to facilitate the development and deployment of these exceptional nucleophiles in complex bond constructions.