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- Title
One‐Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp<sup>3</sup> C−H Imination.
- Authors
Ghosh, Subrata K.; Hu, Mengnan; Comito, Robert J.
- Abstract
The direct replacement of sp3 C−H bonds with simple amine units (−NH2) remains synthetically challenging, although primary aliphatic amines are ubiquitous in medicinal chemistry and natural product synthesis. We report a mild and selective protocol for preparing primary and secondary aliphatic amines in a single pot, based on intermolecular sp3 C−H imination. The first C−H imination of diverse alkanes, this method shows useful site‐selectivity within substrates bearing multiple sp3 C−H bonds. Furthermore, this reaction tolerates polar functional groups relevant for complex molecule synthesis, highlighted in the synthesis of amine pharmaceuticals and amination of natural products. We characterize a unique C−H imination mechanism based on radical rebound to an iminyl radical, supported by kinetic isotope effects, stereoablation, resubmission, and computational modeling. This work constitutes a selective method for complex amine synthesis and a new mechanistic platform for C−H amination.
- Subjects
ALIPHATIC amines; KINETIC isotope effects; SECONDARY amines; AMINATION; PHARMACEUTICAL chemistry; NATURAL products; FUNCTIONAL groups
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 70, p17601
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202102627