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Triple‐Bond Directed Csp 2 −N Bond Formation with N ‐Fluorobenzenesulfonimide as Aminating Source: One‐Step Transformation of Aldehydes into Amines
Author(s) -
Aggarwal Trapti,
Shibata Norio,
Verma Akhilesh K.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903495
Subject(s) - triple bond , chemistry , amination , amine gas treating , quinoline , pyridine , medicinal chemistry , fluorine , combinatorial chemistry , organic chemistry , double bond , catalysis
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)‐λ 2 ‐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.