Donor/donor carbenes are relatively new in the field of carbene chemistry; although applications in C−H and X−H insertion reactions are few in number, they demonstrate exquisite chemo‐ and stereo‐selectivity. Recent reports have shown that C−H, N−H, B−H, O−H, S−H, Si−H, Ge−H, Sn−H and P−H insertion reactions are feasible with a variety of transition metal catalysts, both inter‐ and intramolecularly. Furthermore, high degrees of diastereo‐ and enantioselectivity have been observed in several cases. Methods typically involve the formation of a diazo‐based carbene precursor, but procedures using diazo‐free metal carbenes have been developed with significant success. This Minireview covers transition‐metal catalyzed insertion reactions with donor/donor and donor carbenes, providing context for future developments in this emerging field.

Six-membered ring oxygen and nitrogen heterocycles are formed stereoselectively by C–H insertion of donor/donor carbenes.

Our first-semester organic chemistry class focused on structured group work to enable active learning in class. When Smith College switched to online learning after spring break, the class was adapted to fit into an online learning model while retaining active learning. Using feedback from students, we implemented two tracks, one focused on independent work and one focused on group work. Using Zoom’s breakout rooms, we were able to simulate the full-class and small-group experiences of our in-person class with the help of student learning assistants to facilitate group learning. Slack was introduced for class questions and communications. Student feedback was positive overall and indicated that their perceptions about group work improved over the semester. In the case of in-person classes in the fall, this method might be preferable to a class in which social distancing hampers student-to-student discussion.

Donor/donor carbenes are relatively new in the field of carbene chemistry; although applications in C−H and X−H insertion reactions are few in number, they demonstrate exquisite chemo‐ and stereo‐selectivity. Recent reports have shown that C−H, N−H, B−H, O−H, S−H, Si−H, Ge−H, Sn−H and P−H insertion reactions are feasible with a variety of transition metal catalysts, both inter‐ and intramolecularly. Furthermore, high degrees of diastereo‐ and enantioselectivity have been observed in several cases. Methods typically involve the formation of a diazo‐based carbene precursor, but procedures using diazo‐free metal carbenes have been developed with significant success. This Minireview covers transition‐metal catalyzed insertion reactions with donor/donor and donor carbenes, providing context for future developments in this emerging field.