Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes |
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Authors: | Madhu Ganesh |
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Affiliation: | Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, Maharashtra, India |
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Abstract: | (Z)-α-Bromo-β-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-α,β-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of α-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 α,β-disubstituted nitroethylenes. |
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