A NOVEL PALLADIUM(0) CATALYZED TANDEM 1,3-ALLYL SHIFT AND HECK ARYLATION

Authors
WATSON SP KNOX GR HERON NM
Citation
Sp. Watson et al., A NOVEL PALLADIUM(0) CATALYZED TANDEM 1,3-ALLYL SHIFT AND HECK ARYLATION, Tetrahedron letters, 35(52), 1994, pp. 9763-9766
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
52
Year of publication
1994
Pages
9763 - 9766
Database
ISI
SICI code
0040-4039(1994)35:52<9763:ANPCT1>2.0.ZU;2-O
Abstract
On treatment with Pd(PPh(3))(4) allyl vinyl ether (1) undergoes a Pd(0 ) catalysed 1,3 oxygen to carbon allyl shift to afford alpha-allyl ket one (2). In the presence of both Pd(PPh(3))(4) and base the allyl viny l ether undergoes a Pd(0) catalysed tandem 1,3 allyl shift and intramo lecular Heck arylation to give the spiro indane (3). Mechanistic inves tigations suggest that the 1,3-allyl shift proceeds via a pi-allyl pal ladium intermediate.