958264-27-2Relevant academic research and scientific papers
Intramolecular aminochalcogenation and diamination of alkenes employing N-iodosuccinimide
Zhang, Jun,Zhang, Xuejun,Wu, Weijie,Zhang, Gengtao,Xu, Sheng,Shi, Min
supporting information, p. 1505 - 1509 (2015/03/14)
A NIS-mediated intramolecular diamination and aminosulfuration of alkenes with N-alkyl or N-aryl thioureas is reported. A chiral cyclic thiourea was also synthesized by the methodology. The protocol is also proven to be efficient in the intramolecular dia
An Iodine-Catalyzed Hofmann-L?ffler Reaction
Martínez, Claudio,Mu?iz, Kilian
, p. 8287 - 8291 (2015/07/07)
Iodine reagents have been identified as economically and ecologically benign alternatives to transition metals, although their application as molecular catalysts in challenging C-H oxidation reactions has remained elusive. An attractive iodine oxidation catalysis is now shown to promote the convenient conversion of carbon-hydrogen bonds into carbon-nitrogen bonds with unprecedented complete selectivity. The reaction proceeds by two interlocked catalytic cycles comprising a radical chain reaction, which is initiated by visible light as energy source. This unorthodox synthetic strategy for the direct oxidative amination of alkyl groups has no biosynthetic precedence and provides an efficient and straightforward access to a general class of saturated nitrogenated heterocycles.
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.
Exploring the nickel-catalyzed oxidation of alkenes: A diamination by sulfamide transfer
Muniz, Kilian,Streuff, Jan,Hoevelmann, Claas H.,Nunez, Ana
, p. 7125 - 7127 (2008/09/17)
(Chemical Equation Presented) Nickel can oxidize, too! Nickel (II) salts such as nickel chloride and nickel acetylacetonate catalyze the intramolecular diamination of alkenes with urea and guanidine derivatives as well as sulfamides as nitrogen sources. T
