Iodine(III)-Promoted Intermolecular Diamination of Alkenes

A rapid and productive vicinal diamination of alkenes takes place in the presence of a hypervalent iodine(III) reagent and bissulfonimides as nitrogen sources. A total of more than 60 examples are presented. The reaction is characterized by its robustness and its wide substrate scope: it proceeds se...

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Veröffentlicht in:Chemistry, an Asian journal an Asian journal, 2012-05, Vol.7 (5), p.1103-1111
Hauptverfasser: Souto, José A., González, Yolanda, Iglesias, Alvaro, Zian, Debora, Lishchynskyi, Anton, Muñiz, Kilian
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Sprache:eng
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Zusammenfassung:A rapid and productive vicinal diamination of alkenes takes place in the presence of a hypervalent iodine(III) reagent and bissulfonimides as nitrogen sources. A total of more than 60 examples are presented. The reaction is characterized by its robustness and its wide substrate scope: it proceeds selectively with both terminal and internal alkenes and tolerates a range of functional groups. Se presenta un método eficiente y rápido para llevar a cabo la diaminación de alquenos promovido por especies de iodo(III) hipervalente en presencia de bissulfonilimidas. Una serie de mas de 60 olefinas, tanto en posición terminal como interna, con distinta sustitución demuestran la robustez del método y la elevada tolerancia a grupos funcionales. Diamination of alkenes made easy! The simple combination of the hypervalent iodine reagents PhI(OAc)2 or PhI(OAc)NTs2 with HNTs2 generates an unprecedentedly robust tool for the rapid and productive diamination of alkenes. Reactions include (clockwise from top right) styrenes, terminal alkenes, functionalized and conjugated alkenes, as well as internal alkenes.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201101025