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Synthesis of Diverse Nitrogen Heterocycles via Palladium‐Catalyzed Tandem Azide–Isocyanide Cross‐Coupling/Cyclization: Mechanistic Insight using Experimental and Theoretical Studies
Author(s) -
Ansari Arshad J.,
Pathare Ramdas S.,
Maurya Antim K.,
Agnihotri Vijai K.,
Khan Shahnawaz,
Roy Tapta Kanchan,
Sawant Devesh M.,
Pardasani Ram T.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700928
Subject(s) - nitrene , chemistry , isocyanide , palladium , azide , combinatorial chemistry , atom economy , catalysis , tandem , nitrogen atom , amination , coupling reaction , computational chemistry , photochemistry , organic chemistry , materials science , composite material , group (periodic table)
A rapid and elegant tandem azide–isocyanide cross‐coupling/cyclization protocol has been developed based on a nitrene transfer reaction. The palladium‐catalyzed ligand‐free methodology led to the synthesis of three different heterocyclic scaffolds with excellent atom/step/redox economy. Studies based on first‐principles‐based quantum calculations and control experiments unraveled a concerted process of nitrene transfer reaction on isocyanides, ruling out the metallaaziridine intermediate reported earlier. This finding could pave the way for novel applications of nitrene transfer reactions to generate bioactive heterocycles.