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Facile One‐Pot Assembly of Push–Pull Imines by a Selective C–F Substitution Process in Aryl Fluorides
Author(s) -
Anga Srinivas,
Chandra Shubhadeep,
Sarkar Pallavi,
Das Shubhajit,
Mandal Debdeep,
Kundu Abhinanda,
Rawat Hemant,
Schulzke Carola,
Sarkar Biprajit,
Pati Swapan K.,
Chandrasekhar Vadapalli,
Jana Anukul
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001344
Subject(s) - chemistry , substituent , imine , reagent , aryl , nucleophilic substitution , combinatorial chemistry , nucleophilic aromatic substitution , nucleophilic addition , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
Herein, we report the synthesis of a series of push–pull imines by considering cyclic diamino substituent at the C‐centre and fluoroaryl substituent at the N‐centre. This has been achieved by a selective aromatic nucleophilic substitution of different fluoroarenes by N ‐H‐substituted N ‐heterocyclic imines (NHIs) at ambient conditions without any additional reagent. Solid‐state molecular structure analysis reveals the elongation of the central C–N bond of the imine functionality, which is consistent with the push–pull nature of these imines. The push–pull nature of these imines is further validated by computational studies.