Triple‐Bond Directed Csp²−N Bond Formation with N‐Fluorobenzenesulfonimide as Aminating Source: One‐Step Transformation of Aldehydes into Amines

Abstract

A metal‐free, versatile triple‐bond directed approach for the decarbonylative C−H amination of ortho‐alkynyl quinoline/pyridine aldehydes using N‐fluorobenzenesulfonimide as nitrogen source under mild reaction conditions has been described. The designed reaction strategy was triggered by trapping of fluorine by base with subsequent attack of bis(phenylsulfonyl)‐λ2‐azane on the carbonyl carbon of a heterocycle, which was gradually converted into the corresponding amine through a Curtius type rearrangement. This protocol provides a one‐step approach for the conversion of aldehydes into amines in good yields. The synthesized amines were successfully transformed into biologically important pyrroloquinolines/pyridines.

Unveiling the Three-Component Phosphonylation on Alkynylaldehydes: Toolbox toward Fluorescent Molecules

“…Recently, Peng and co-workers have reported the enantioselective synthesis of cyclic α-amino phosphonates using chiral silver spirocyclic phosphate as the catalyst . Considering the importance of small heterocyclic drug molecules and our ongoing chemistry using o -alkynylaldehydes, herein we have reported the synthesis of phosphine oxide embedded − N and − O heterocycles under mild reaction conditions (Scheme b).…”

Ligand-free copper-catalyzed C(sp3)–H imidation of aromatic and aliphatic methyl sulfides with N-fluorobenzenesulfonimide

“…1 ). 3 Typical methods for C–N bond formation include Buchwald–Hartwig, Ullmann–Goldberg and Chan–Evans–Lam imidations, which are mostly transition metal catalyzed, and require prefunctionalization of starting materials. 4 Recently, a more concise and atom-economic alternative to such imidations has been investigated by direct C–H imidation of oxidized nitrogen reagents and carbon nucleophiles.…”