What is it about?
A metal-free decarbonylative C-H amination of ortho-alkynyl quinoline/pyridine aldehyde using N-Fluorobenzenesulfonimide as nitrogen source under mild reaction conditions has been described. The designed reaction was triggered by trapping of fluorine through the nitrogen atom of heterocycle followed by a chemoselective attack of bis (phenylsulfonyl)-λ2-azane on carbonyl carbon which gradually converted to an amine via Curtius type rearrangement. This protocol provides a one-step approach for the conversion of an aldehyde to amine in good yields. The synthesized amines compounds were successfully transformed into biologically important pyrroloquinolines /pyridines.
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Why is it important?
we have demonstrated a novel approach for the direct conversion of ortho- alkynyl quinoline/pyridyl-3-aldehydes into ortho-alkynyl quinoline/pyridyl-3-amine using N-fluorobenzenesulfonamide as nitrogen source under basic condition.
Perspectives
A metal-free versatile triple bond directed approach for the decarbonylative C-H amination of ortho-alkynyl quinoline/pyridine aldehyde using N-Fluorobenzenesulfonimide as nitrogen source under mild reaction conditions has been described.
Akhilesh Verma
University of Delhi
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This page is a summary of: Triple‐Bond Directed Csp
2
−N Bond Formation with
N
‐Fluorobenzenesulfonimide as Aminating Source: One‐Step Transformation of Aldehydes into Amines, Chemistry - A European Journal, November 2019, Wiley,
DOI: 10.1002/chem.201903495.
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