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

摘要: 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 high yield (up 95%) complete specificity. Similar α-bromonitroethylenes terminal acetylenes (Sonogashira coupling) provides a novel route (E)-nitroenynes. These Pd-catalyzed methods offer convenient stereospecific entry into diverse array synthetically biologically useful α,β-disubstituted nitroethylenes.