Substitution Effects of Hypervalent Iodine(III) Reagents in the Diamination of Styrene

The influence of electronic parameters on the reaction performance of hypervalent iodine­(III) reagents in the vicinal diamination of styrene has been investigated. It demonstrates the influence of the relative electron density on the aryl substituent of the hypervalent iodine reagent. In these case...

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Veröffentlicht in:Journal of organic chemistry 2016-07, Vol.81 (14), p.6118-6122
Hauptverfasser: Romero, R. Martín, Souto, José A, Muñiz, Kilian
Format: Artikel
Sprache:eng
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Zusammenfassung:The influence of electronic parameters on the reaction performance of hypervalent iodine­(III) reagents in the vicinal diamination of styrene has been investigated. It demonstrates the influence of the relative electron density on the aryl substituent of the hypervalent iodine reagent. In these cases, compounds with donor substituents outperform the corresponding acceptor-substituted systems. In line with this observation, a rapid enantioselective diamination was observed for a preformed chiral bisimidoiodine­(III) reagent. For the first time, X-ray structural data could be obtained for an isolated chiral bisimidoiodine­(III).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01070