ACKNOWLEDGMENTWe graciously acknowledge the chemistry department at the University of Rhode Island for providing generous funding. Ms. Nicole Cook is also thanked for her editorial suggestions and expertise.

A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.

A new approach for the direct amination of 2-phenylpyridine derivatives using a diphthalimide-iodane and copper triflate has been developed. A series of different 2-phenylpyridine derivatives were aminated with yields up to 88%. Mechanistic investigations indicate that the reaction proceeds via a copper-mediated single electron transfer.

A contemporary approach to the synthesis and purification of several UV-active dipeptides has been developed for the second-year organic laboratory. This experiment exposes students to the important technique of solution-phase peptide synthesis and allows an instructor to highlight the parallel between what they are accomplishing in the laboratory to the advancements being made in the pharmaceutical industry. By illustrating the importance of protecting group strategy and stereochemistry preservation, while also reinforcing the various separatory and purification techniques learned throughout the typical laboratory course, this experiment serves as an excellent candidate for a capstone project that assesses students' mastery of important techniques learned in an introductory organic laboratory course.