85083-59-6Relevant articles and documents
A new method for the preparation of (arylsulfonyliminoiodo)benzenes
Besenyei, Gabor,Nemeth, Sandor,Simandi, Laszlo I.
, p. 6105 - 6106 (1993)
(Arylsulfonyliminoiodo)benzenes (3) can be prepared in 52-92% yield via the reaction of dimethoxyiodobenzene (1) with the corresponding arylsulfonamide in MeOH or CH2Cl2 at room temperature.
One-Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp3 C?H Imination
Comito, Robert J.,Ghosh, Subrata K.,Hu, Mengnan
supporting information, p. 17601 - 17608 (2021/11/03)
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.
