ChemInform Abstract: Speedy and Clean Hypervalent Iodine/Nitroxyl Radical Mediated Oxidation of Alcohols Using Recyclable Adamantane Reagent with Highly Active 2‐Azaadamantane‐N‐oxyl Organocatalyst.

Dohi, Tomotaka; Kamitanaka, Tohru; Mochizuki, Eisuke; Ito, Minoru; Kita, Yasuyuki

doi:10.1002/chin.201316027

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reduced forms of these reagents are recyclable by a simple filtration of the solution in methanol. 322,323,1583,1584 In particular, the oxidation of alcohols to carbonyl compounds by 1,3,5,7-tetraphenyladamantanebased hypervalent iodine(III) reagent 730 in the presence of nitroxy radical AZADO has been reported. 1583,1584 This methodology can be applied to the nonracemic oxidation of an optically active alcohol 745 to the enolizable ketone 746 (Scheme 214).…”

Section: Recyclable Nonpolymeric Iodine(iii) Reagentsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

View full text Add to dashboard Cite

The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

show abstract