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Para ‐Selective Cyanation of Arenes by H‐Bonded Template
Author(s) -
Pimparkar Sandeep,
Bhattacharya Trisha,
Maji Arun,
Saha Argha,
Jayarajan Ramasamy,
Dutta Uttam,
Lu Gang,
Lupton David W.,
Maiti Debabrata
Publication year - 2020
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.202001368
Subject(s) - moiety , cyanation , selectivity , nitrile , reusability , substrate (aquarium) , surface modification , combinatorial chemistry , nanotechnology , chemistry , materials science , computer science , organic chemistry , catalysis , oceanography , software , programming language , geology
The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work, we demonstrate the para ‐selective introduction of versatile nitrile moiety, enabled by a detachable and reusable H‐bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools, which heralds the inception of para ‐deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.