ANOMERIC AMIDE

N-Pivaloyloxy-N-Benzyloxy-4-Trifluoromethylbenzamide was developed by our laboratory (Nature 2021, 593, 223–227) as a uniquely effective reagent for the generation of isodiazenes directly from secondary and primary amines at or near room temperature. This reagent has since found wide application in a range of deletion, deamination, and deaminative functionalization reactions by our group and others:
(1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12)

Available from Enamine: https://enaminestore.com/catalog/EN300-33050767

ELECTROPHILIC AMINATION

O-sulfonylhydroxylamine derivatives are well-known electrophilic aminating reagents, with the mesitylsulfonyl derivative, MSH, serving as a widely-used N-aminating reagent in heterocycle synthesis. However, we have found that for weakly nucleophilic heterocycles, more reactive derivatives are required.  While the free -NH₂ species is typically not isolable for electron-withdrawn sulfonyl groups, we have found deprotection of the N-Boc derivative is an effective means to generate the requisite species in situ, as many weakly nucleophilic heterocycles are also weak bases. This reagent figured prominently in our S-to-NR atom replacement of thiazoles (Nature 2025, 641, 646–652), and is being applied to further transformations in our laboratory.

Available from Enamine: https://enaminestore.com/catalog/EN300-52272785

N-BROMOCAPROLACTAM

Selective oxidation of an azepine intermediate is central to our reported C-to-N replacement reaction of aryl azides (Science 2023, 381(6665), 1474-1479). N-Bromocaprolactam was found to provide superior yields to traditional oxidants, allowing the preparation of pyridines by atom replacement.

Available from Enamine: https://enaminestore.com/catalog/EN300-1717385