On the use of tandem allylic acetate isomerisation and ring-closing metathesis with palladium(0) phosphine complexes and ruthenium benzylidenes as orthogonal catalysts

Citation
Dc. Braddock et Aj. Wildsmith, On the use of tandem allylic acetate isomerisation and ring-closing metathesis with palladium(0) phosphine complexes and ruthenium benzylidenes as orthogonal catalysts, TETRAHEDR L, 42(18), 2001, pp. 3239-3242
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
18
Year of publication
2001
Pages
3239 - 3242
Database
ISI
SICI code
0040-4039(20010430)42:18<3239:OTUOTA>2.0.ZU;2-2
Abstract
Attempted tandem allylic acetate isomerisation and ring-closing metathesis using combinations of palladium(0)/Grubbs' catalyst/PPh3 led to either ally lic isomerisation or ring-closing metathesis but not both in tandem. The ef fect was traced to deactivation of Grubbs' catalyst by added PPh3 and poiso ning of the Pd(0) by the necessarily released PCy3 (Cy=cyclohexyl) from Gru bbs' catalyst. Successful tandem isomerisation/ring-closing metathesis was achieved by the use of palladium(0)/PPh3 systems in conjunction with a PCy3 free olefin metathesis catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.