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Study on fluoroalkylation and fluoroalkoxylation: 19. Iridium(I)‐catalyzed reaction of fluoroalkyl iodides with alkenes and alkynes
Author(s) -
QingYun Chen,
YaBo He,
ZhenYu Yang
Publication year - 1988
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19880060210
Subject(s) - chemistry , iridium , adduct , tetrahydrofuran , catalysis , triphenylphosphine , medicinal chemistry , polymer chemistry , ether , photochemistry , addition reaction , organic chemistry , solvent
Fluoroalkyl iodides reacted with alkenes in the presence of hydridocarbonyltris(triphenylphosphine)iridium (I) to give the corresponding adducts in excellent yields under the mild conditions. Fluoroalkyl iodides reacted also with alkynes to afford E isomer of adducts predominantly. Addition of free radical inhibitor or single electron transfer scavenger to the reaction mixture partially suppressed the reaction. Diallyl ether could trap the fluoroalkyl radical to afford tetrahydrofuran derivative. XPS showed that the valence of Ir (I) rised at the end of the reaction. All findings seem to indicate that the reaction involves a free radical chain mechanism initiated by Ir (I).