A New Method for Intramolecular Chloroamination of Unfunctionalized Olefins

Abstract

A new method for the intramolecular chloroamination of unfunctionalized olefins is reported. The reactions were carried out at room temperature for 3 h using hydrated copper(II) chloride as both promoter and chlorine source, and the corresponding vincinal haloamines were obtained in good isolated yields.

n‐Bu4NI/K2S2O8‐Mediated C−N Coupling Between Aldehydes and Amides

“…When an aryl aldehyde bears an electron‐donating group at either the para or ortho position of the formyl group, such as p ‐anisaldehyde, o ‐anisaldehyde, p ‐tolualdehyde, 4‐hydroxybenzaldehyde, 2‐hydroxybenzaldehyde and thiophene‐2‐carbaldehyde, the reaction all exclusively led to the transformylation product 2 (Table 2). Among all the aryl aldehydes examined, p ‐anisaldehyde afforded the highest yield of 2 [15] . In the cases where the transformylation products were obtained in low yields, the unreacted amides were recovered.…”

Isocoumarins: General Aspects and Recent Advances in their Synthesis

“…Liu and co‐workers reported another Rh(III)‐catalyzed intermolecular redox‐neutral C–H activation and annulation reaction of O ‐benzylhydroxylamines and alkynes to provide isocoumarin derivatives where the O−N bond of the hydroxylamine acted as an internal oxidant [Scheme , Eq. (1)] …”

Catalyst‐free Chloroamination Cyclization Cascade with Sodium Hypochlorite: from N‐(Pentenyl)sulfonylamides to 2‐(1‐Chloromethyl)pyrrolidines

“…In 2013, Li et al demonstrated that copper(II) chloride could be used as both a chlorine source and a catalyst for the chloroamination of benzylated aminoalkenes. [16] A year later, the same research group developed a metal-free method using (diacetoxyiodo)benzene as a catalyst in the presence of pyridinium chloride. [17] An alternative method to synthesize 2chloromethylpyrrolidines involves the generation of an amidyl radical from N-chloroamines, [18] which could be subjected to cyclization in the presence of copper, [19] or titanium-based catalysts.…”