Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C–C Activation/Cycloaddition between Isatins and Isocyanates

Abstract

The first decarbonylative cycloaddition of less-strained cyclic ketones (isatins) with isocyanates is reported. Initiated by C–C activation, this distinct [5−2+2] transformation provides a rapid entry to access various benzimidazolidinone derivatives, through which a wide range of isocyanates can be efficiently coupled with broad functional group tolerance. A modified one-pot process, combining Curtius rearrangement and C–C activation, was also achieved by using acyl azides as the starting materials. Detailed mechanistic study revealed a surprising double-decarbonylative reaction pathway. The novel reactivity discovered in this basic research is expected to shed light on developing new heterocycle formation methods through a C–C/isocyanate coupling.

Heterostructure CoS/NC@MoS2Hollow Spheres for High‐Performance Hydrogen Evolution Reactions and Lithium‐ION Batteries

“…Metal-organic frameworks (MOFs), a class of multifunctional materials with tunable nanostructure, high porosity and large specific surface area have attracted great interest in a wide range. [16] MOFs could be used for gas storage and separation, [17] catalysis, [18] sensors [19] and so on. MOFs constructed by different metal ions and organic ligand equipped with different properties could satisfy various demands.…”

“Cut and Sew” Transformations via Transition-Metal-Catalyzed Carbon–Carbon Bond Activation

“…114 Use of electron-deficient ligands such as AsPh 3 proved crucial to provide the benzimidazolidinone products 120 in excellent yields. A range of functional groups were found compatible.…”

Recent Progress in the Removal of Heavy Metal Ions from Water Using Metal‐Organic Frameworks

“…These materials can be synthesized normally at ambient temperatures of up to 220°C, at atmospheric pressure, and in the pH range of 1-10 by various methods such as solvo(hydro)thermal, mechanochemical, sonochemical, electrochemical, layer-by-layer growth, and microwave. [17,[31][32][33] The infinite combinations of metal nodes and organic linkers can yield new frameworks having diverse constructions along with fascinating properties, such as heterogeneous catalysis and photocatalysis, [34] drug delivery, [35] energy storage, [36] gas storage, [37] sensing, [38][39][40][41] and adsorption [42] and detection of hazardous materials. [43][44][45] Among the reported adsorbents, MOFs are considered as one of the most encouraging materials for removal of the HMIs, due to their high design capability, large surface areas, optimal chemical as well as physical properties, high porosity and intelligent architecture.…”