2219-34-3Relevant articles and documents
Selenium-assisted one-pot synthesis of carbodiimides from isocyanides and primary amines
Fujiwara, Shin-Ichi,Matsuya, Takahiro,Maeda, Hajime,Shin-Ike, Tsutomu,Kambe, Nobuaki,Sonoda, Noboru
, p. 75 - 76 (1999)
Reaction of isocyanides with primary amines in the presence of selenium and DBU, followed by introduction of molecular oxygen in refluxing THF affords carbodiimides in high yields.
Carbodiimide Synthesis via Ti-Catalyzed Nitrene Transfer from Diazenes to Isocyanides
Beaumier, Evan P.,McGreal, Meghan E.,Pancoast, Adam R.,Wilson, R. Hunter,Moore, James T.,Graziano, Brendan J.,Goodpaster, Jason D.,Tonks, Ian A.
, p. 11753 - 11762 (2019)
Simple Ti imido halide complexes such as [Br2Ti(NtBu)py2]2 are competent catalysts for the synthesis of unsymmetrical carbodiimides via Ti-catalyzed nitrene transfer from diazenes or azides to isocyanides. Both alkyl and aryl isocyanides are compatible with the reaction conditions, although product inhibition with sterically unencumbered substrates sometimes limits the yield when diazenes are employed as the oxidant. The reaction mechanism has been investigated both experimentally and computationally, wherein a key feature is that the product release is triggered by electron transfer from an η2-carbodiimide to a Ti-bound azobenzene. This ligand-to-ligand redox buffering obviates the need for high-energy formally TiII intermediates and provides further evidence that substrate and product "redox noninnocence" can promote unusual Ti redox catalytic transformations.
Direct Assembly of Polysubstituted Propiolamidinates via Palladium-Catalyzed Multicomponent Reaction of Isocyanides
Li, Meng,Fang, Songjia,Zheng, Jia,Jiang, Huanfeng,Wu, Wanqing
supporting information, p. 8439 - 8443 (2019/10/16)
A straightforward approach for the assembly of different polysubstituted propiolamidnates via palladium-catalyzed multicomponent reaction of isocyanides, haloalkynes, and amines has been reported in which the C(sp)-C(sp2) and C(sp2)a
Synthesis of Diverse Nitrogen Heterocycles via Palladium-Catalyzed Tandem Azide–Isocyanide Cross-Coupling/Cyclization: Mechanistic Insight using Experimental and Theoretical Studies
Ansari, Arshad J.,Pathare, Ramdas S.,Maurya, Antim K.,Agnihotri, Vijai K.,Khan, Shahnawaz,Roy, Tapta Kanchan,Sawant, Devesh M.,Pardasani, Ram T.
supporting information, p. 290 - 297 (2017/12/07)
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. (Figure presented.).
