Premium
An efficient catalytic system for cyclocarbonylation of terpenes into lactones
Author(s) -
Nguyen Duc Hanh,
Hebrard Frédéric,
Duran Josep,
Polo Alfonso,
Urrutigoíty Martine,
Kalck Philippe
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.727
Subject(s) - chemistry , lactone , allylic rearrangement , catalysis , terpene , geraniol , alcohol , butane , organic chemistry , carbonylation , ligand (biochemistry) , citronellol , palladium , receptor , carbon monoxide , biochemistry , chromatography , essential oil
Three different kinds of representative monoterpenic alcohol are involved in the palladium‐catalysed cyclocarbonylation reaction. Lactone formation is shown to occur when cyclic ( 1 ), tertiary ( 3 ) and primary allylic alcohol ( 7 ) functions are reacted, in the presence of CO with [HPd(SnCl 3 )L 2 ] as the active catalytic species. Good yields and selectivities can easily be reached for isopulegol ( 1 ), and dihydromyrcenol ( 3 ). However, more modest results are obtained for the functionalization of geraniol into the original lactone ( 9 ). This lactone can be largely favoured by using a basic chelating diphosphine ligand such as 1,4‐bis(diphenylphosphino)butane. Copyright © 2005 John Wiley & Sons, Ltd.