Selective delivery of an N-nucleophile onto an alkyl radical is a challenging step in redox catalysis. In this work, di-tert-butyl hydrazodiformate was found to be a unique effective amination reagent in Cu-catalyzed C(sp3)–N bond formation reactions that involve alkyl radical intermediates. This method is applicable to both electron-deficient and electron-rich radicals, and we were thus able to achieve the direct C–N coupling of activated bromides, as well as the carboamination of general alkenes based on this chemistry. Mechanistic studies suggest that the hydrazodiformate forms a reducing dinuclear complex with Cu and the ligand which, upon 1e-oxidation, turns into an open-shell species with the major spin density on N atoms. With the assistance of a ligand, this species can selectively deliver the hydrazine moiety onto an alkyl radical (prior to halide transfer), leading to the formation of a C(sp3)–N bond. The products obtained with this amination method could be easily deprotected to afford alkyl hydrazines and further derived to primary amines or N-heterocycles.

A photoredox-enabled alkylative dearomatization of protected anilines is reported. Under Ir catalysis and light irradiation, an N-carbamoyl-protected aniline and an α-bromocarbonyl compound could be simultaneously activated, and the two resulting radical species then recombine with each other to afford a dearomatized cyclohexadienone imine as the major product. A series of such imines with contiguous quaternary carbon centers were prepared, which can be further converted into cyclohexadienones, cyclohexadienols, and cyclohexyl amines.

A 61-year-old male with no past medical history presented with intense abdominal pain for three days, associated with hematochezia, nausea, and non-bloody vomiting. CT scan of the abdomen showed distended small bowel, diffuse lymphadenopathy, and intussusception of the distal ileum into the cecum with obstruction. Ileocolic resection and histopathological staining confirmed the diagnosis of follicular lymphoma and appropriate treatment was initiated. Intussusception is a condition that involves the invagination of the proximal segment of a bowel tract into its contiguous distal segment as a result of enthusiastic or impaired peristalsis. Only 5% of the total intussusception cases are found in adults. Most cases in adults are caused by pathological lead points which can be benign or malignant. Lymphomas rarely present with intussusception and follicular lymphomas are even less common. To the best of our knowledge, there have only been a few such cases of follicular lymphomas with the initial presentation of intussusception. In this article, we present a rare case of follicular lymphoma presenting as intussusception. Considering lymphomas as a cause of intussusception in adults can decrease diagnostic delays and guide treatment.