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- W4386830887 abstract "Electrophilic halogenation is a widely-used tool employed by medicinal chemists to either pre-functionalize molecules for further diversity or incorporate a halogen atom in drugs or drug-like compounds to solve metabolic problems or modulate off-target effects. Current methods to increase the power of halogenation rely either on the invention of new reagents or activating commercially available reagents with various additives such as Lewis/Brønsted acids, Lewis bases and hydrogen bonding activators. There is a high demand for new reagents that can halogenate otherwise unreactive compounds under mild conditions. Herein we report the invention a new class of powerful halogenating reagents based on anomeric amides, taking advantage of the energy stored in the pyramidalized nitrogen of N-X anomeric amides as a driving force. These robust halogenating methods are compatible with a variety of functional groups and heterocycles, as exemplified on over 50 compounds (including 13 gram-scale examples and 1 flow chemistry scale-up). Their high halogenating prowess is also demonstrated in other reactivity contexts. A DFT computational study supports the defining role of the anomeric amide motif." @default.
- W4386830887 created "2023-09-19" @default.
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- W4386830887 date "2023-09-18" @default.
- W4386830887 modified "2023-09-26" @default.
- W4386830887 title "Introducing N-X Anomeric Amides: Powerful Electrophilic Halogenation Reagents" @default.
- W4386830887 doi "https://doi.org/10.26434/chemrxiv-2023-z15zd" @default.
- W4386830887 hasPublicationYear "2023" @default.
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