Stereoselective Nitration of Olefins with (BuONO)-Bu-t and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions

Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-fre...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 13; pp. 3384 - 3387
Main Authors Maity, Soham, Naveen, Togati, Sharma, Upendra, Maiti, Debabrata
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.07.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
BETA-NITROSTYRENES
CONJUGATED NITROALKENES
NITROGEN MONOXIDE
CONVENIENT
N BOND FORMATION
TERT-BUTYL NITRITE
DERIVATIVES
ARYLBORONIC ACIDS
C-H
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Summary:Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.
ISSN:1523-7060
DOI:10.1021/ol401426p