Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-lambda(3)-bromane Generated in Situ under Metal-Free Conditions

Ligand exchange of p-CF3C6H4BrF2 with acetoxy groups using AcOH and Ac2O affords (diacetoxybromo)benzene in a high yield, which undergoes azirldination of alkenes In the presence of TfNH2 and sulfamate esters in one pot under mild conditions. The azirldination with TfNH2 proceeds stereospecifically...

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Published inOrganic letters Vol. 13; no. 20; pp. 5428 - 5431
Main Authors Hoque, Md. Mahbubul, Miyamoto, Kazunori, Tada, Norihiro, Shiro, Motoo, Ochiai, Masahito
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 21.10.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
AMINATION
SULFONYLIMINO-LAMBDA-BROMANE
MANGANESE PORPHYRINS
AMIDATION
CHEMISTRY
RUTHENIUM
SULFONAMIDES
C-H BONDS
HIGHLY EFFICIENT
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Summary:Ligand exchange of p-CF3C6H4BrF2 with acetoxy groups using AcOH and Ac2O affords (diacetoxybromo)benzene in a high yield, which undergoes azirldination of alkenes In the presence of TfNH2 and sulfamate esters in one pot under mild conditions. The azirldination with TfNH2 proceeds stereospecifically with retention of stereochemistry of olefins at room temperature using limiting amounts of olefins under transition-metal-free conditions. The one-pot aziridination procedure using sulfamate esters can be applied to the Intramolecular versions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201868n