PALLADIUM-PROMOTED INTRAMOLECULAR ADDITION OF AN ARYL IODIDE TO A NITROALKENE

Authors
DENMARK SE SCHNUTE ME
Citation
Se. Denmark et Me. Schnute, PALLADIUM-PROMOTED INTRAMOLECULAR ADDITION OF AN ARYL IODIDE TO A NITROALKENE, Journal of organic chemistry, 60(4), 1995, pp. 1013-1019
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
4
Year of publication
1995
Pages
1013 - 1019
Database
ISI
SICI code
0022-3263(1995)60:4<1013:PIAOAA>2.0.ZU;2-I
Abstract
Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd(OAc)(2) (1.0 equiv), triphenylphosph ine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 degrees C to afford exocyclic 2,2-disubstituted-1-nitroalkene (Z)-2 as a single geo metrical isomer (43%) along with the corresponding saturated nitroalka ne 10 (40%). Subsequent selenylation of the nitroalkane, oxidative eli mination, and olefin isomerization afforded (Z)-2 in 70% yield. The in fluence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.