53370-98-2Relevant articles and documents
Photocatalytic Difunctionalization of Vinyl Ureas by Radical Addition Polar Truce–Smiles Rearrangement Cascades
Abrams, Roman,Clayden, Jonathan
supporting information, p. 11600 - 11606 (2020/05/25)
We report tandem alkyl-arylations and phosphonyl-arylations of vinyl ureas by way of a photocatalytic radical-polar crossover mechanism. Addition of photoredox-generated radicals to the alkene forms a new C?C or C?P bond and generates a product radical adjacent to the urea function. Reductive termination of the photocatalytic cycle generates an anion that undergoes a polar Truce–Smiles rearrangement, forming a C?C bond. The reaction is successful with a range of α-fluorinated alkyl sodium sulfinate salts and diarylphosphine oxides as radical precursors, and the conformationally accelerated Truce–Smiles rearrangement is not restricted by the electronic nature of the migrating aromatic ring. Formally the reaction constitutes an α,β-difuctionalisation of a carbon–carbon double bond, and proceeds under mild conditions with visible light and a readily available organic photocatalyst. The products are α,α-diaryl alkylureas typically functionalized with F or P substituents that may be readily converted into α,α-diaryl alkylamines.
Cooperative Lewis Acid/Cp?CoIII Catalyzed C-H Bond Activation for the Synthesis of Isoquinolin-3-ones
Kim, Ju Hyun,Gre?ies, Steffen,Glorius, Frank
supporting information, p. 5577 - 5581 (2016/05/09)
A facile route toward the synthesis of isoquinolin-3-ones through a cooperative B(C6F5)3- and Cp?CoIII-catalyzed C-H bond activation of imines with diazo compounds is presented. The inclusion of a catalytic amount of B(C6F5)3 results in a highly efficient reaction, thus enabling unstable NH imines to serve as substrates. CoIII-operative catalysis: The first facile route toward the synthesis of isoquinolin-3-ones through cooperative C-H bond activation with B(C6F5)3 (BCF in picture) and Cp?CoIII (Cp?=C5Me5) is presented. The newly developed catalytic system is highly reactive, thus unstable NH imines can serve as substrates.
Geometry-selective synthesis of e or Z N -vinyl ureas (N -carbamoyl enamines)
Lefranc, Julien,Tetlow, Daniel J.,Donnard, Morgan,Minassi, Alberto,Galvez, Erik,Clayden, Jonathan
supporting information; experimental part, p. 296 - 299 (2011/03/22)
N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vi