1000848-82-7Relevant articles and documents
3-(Triflyloxy)benzynes Enable the Regiocontrolled Cycloaddition of Cyclic Ureas to Synthesize 1,4-Benzodiazepine Derivatives
Kaneko, Hideki,Ikawa, Takashi,Yamamoto, Yuta,Arulmozhiraja, Sundaram,Tokiwa, Hiroaki,Akai, Shuji
, p. 943 - 948 (2018)
A versatile synthesis of 1,4-benzodiazepine derivatives through the reaction of various 3-(trifluoromethanesulfonyloxy)benzynes with N -(p -toluenesulfonyl)imidazolidin-2-ones is reported. This reaction system provides a 1,4-benzodiazepine bearing a trifluoromethanesulfonyloxy group as a single regioisomer among the four possible regioisomers.
Intramolecular diamination and alkoxyamination of alkenes with N-sulfonyl ureas employing N-iodosuccinimide
Li, Hao,Widenhoefer, Ross A.
experimental part, p. 4827 - 4831 (2010/08/20)
Reaction of N-δ-alkenyl-N′-sulfonyl urea 1 with N-iodosuccinimde (NIS; 2 equiv) and a catalytic amount of AgOTf (20 mol %) at room temperature led to intramolecular alkoxyamination to form bicyclic isourea 2a in 95% isolated yield. In comparison, reaction
Oxidative interception of the hydroamination pathway: A gold-catalyzed diamination of alkenes
Iglesias, Alvaro,Muniz, Kilian
experimental part, p. 10563 - 10569 (2010/04/05)
A complimentary diamination of alkenes by using homogeneous gold catalysts is described. The reaction is one of very few examples of homogeneous gold oxidation catalysis and proceeds with high selectivity under mild conditions. Individual steps of the sug
Oxidative diamination of alkenes with ureas as nitrogen sources: Mechanistic pathways in the presence of a high oxidation state palladium catalyst
Muniz, Kilian,Hoevelmann, Claas H.,Streuff, Jan
, p. 763 - 773 (2008/09/19)
A first palladium-catalyzed intramolecular diamination of unfunctionalized terminal alkenes has recently been reported. This study investigates the details of its mechanistic course based on NMR titration, kinetic measurements competition experiments, and deuterium labeling. It concludes a two-step procedure consisting of syn-aminopalladation with an unligated palladium(II) catalyst state followed by oxidation to palladium(IV) and subsequent C-N bond formation to give the final products as cyclic diamines. Related reactions employing sulfamides give rise to aminoalkoxy-functionalization of alkenes. This process was investigated employing deuterated alkenes and found to follow an identical mechanism where stereochemistry is concerned. It exemplifies the importance of cationic palladium(IV) intermediates prior to the final reductive elimination from palladium and proves that the nucelophile for this step stems from the immediate coordination sphere of the palladium(IV) precursor. These results have important implications for the general development of alkene 1,2-difunctionalization and for the individual processes of aminopalladation and palladium-catalyzed Calkyl-N bond formation.