Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.

Direct enantioselective synthesis of chiral aza-quaternary carbon indolenines through the dearomative electrophilic hydrazination of 2,3-disubstituted indoles has been achieved. This catalytic asymmetric strategy leads to the efficient construction of a series of enantioenriched aza-quaternary carbon indolenines in high yields and excellent stereoselectivities. The synthetic practicality of this reaction has been demonstrated by the enantioselective modification and derivatization of drug molecules. In-situ infrared and density functional theory calculations suggest that our catalytic system could overcome the background reaction to achieve effective enantioselective dearomatization.

Student-centered teaching has become increasingly common in higher education as researchers have demonstrated its efficacy in recent decades. Herein, we hope to establish an efficient problem-based learning (PBL) method, which can help upperdivision students learn organic chemistry content by combining teaching materials, experimental literature, and computational methods in a self-directed way, systematically and deeply. We aim to cultivate the critical-thinking skills of students and to expand modern research methods to analyze, predict, and understand organic chemical processes. On the basis of such goals and ideas, we take the practical Friedel−Crafts alkylation reaction as a model reaction. We focus on two key points, the pre-equilibrium and the rate-determining step (RDS). In combination with the textbook knowledge and DFT calculation method, we attempt to promote the upper-division students to further discuss and understand reaction details, including kinetic-controlled reactions, the Hammond−Leffler postulate, and the Curtin−Hammett principle, etc. Following this approach, we achieve our goals to discuss the Friedel−Crafts alkylation reaction and provide juniors with a deep understanding of the carbon−carbon bond formation reaction. Furthermore, students initially master the DFT calculation method and make a direct connection between experimental observations and computational results. This approach activates students' study interests to further use core ideas of structures and bonding to rationalize complex chemical reaction phenomena for their future learning career.