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Stereospecific approach to alpha,beta-disubstituted nitroalkenes via coupling of alpha-bromonitroalkenes with boronic acids and terminal acetylenes

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Title Stereospecific approach to alpha,beta-disubstituted nitroalkenes via coupling of alpha-bromonitroalkenes with boronic acids and terminal acetylenes
 
Creator GANESH, MADHU
NAMBOOTHIRI, IRISHI NN
 
Subject sonogashira coupling
alpha-bromonitroalkenes
acids
terminals
 
Description (Z)-alpha-Bromo-beta-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-alpha,beta-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar
coupling of a-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful alpha,beta-disubstituted nitroethylenes.
Copyright to Elsevier Publisher
 
Publisher Elsevier
 
Date 2007-12-20T09:01:49Z
2011-11-25T12:19:42Z
2011-12-26T13:05:20Z
2011-12-27T05:51:49Z
2007-12-20T09:01:49Z
2011-11-25T12:19:42Z
2011-12-26T13:05:20Z
2011-12-27T05:51:49Z
2007-11-26
 
Type Article
 
Identifier Tetrahedron 63(48), 11973–983
0040-4020
http://dx.doi.org/10.1016/j.tet.2007.09.012
http://hdl.handle.net/10054/59
http://dspace.library.iitb.ac.in/xmlui/handle/10054/59
 
Language en