Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 56, Pages 13971-13976Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202102635
Keywords
amination; heterocycles; iodine; radical; synthetic methods
Categories
Funding
- JSPS KAKENHI [19H02716, 20K05511]
- Grants-in-Aid for Scientific Research [20K05511, 19H02716] Funding Source: KAKEN
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A new transition-metal-free method using t-BuOI or NIS was reported for the construction of 1,3-diamine structures, enabling secondary non-benzylic and tertiary C-H amination reactions to proceed. Mechanistic investigations revealed different pathways for amination reactions using t-BuOI or NIS.
1,3-Diamines are an important class of compounds that are broadly found in natural products and are also widely used as building blocks in organic synthesis. Although the intramolecular C-H amination of N-alkylsulfamide derivatives is a reliable method for the construction of 1,3-diamine structures, the majority of these methods involve the use of a transition-metal catalyst. We herein report on a new transition-metal-free method using tert-butyl hypoiodite (t-BuOI) or N-iodosuccinimide (NIS), enabling secondary non-benzylic and tertiary C-H amination reactions to proceed. The cyclic sulfamide products can be easily transformed into 1,3-diamines. Mechanistic investigations revealed that amination reactions using t-BuOI or NIS each proceed via different pathways.
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