THE USE OF ORTHO-CHELATING ARENETHIOLATE NONTRANSFERABLE GROUPS IN THE COPPER(I) CATALYZED SELECTIVE ALPHA-SUBSTITUTION OR GAMMA-SUBSTITUTION OF ACYCLIC ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS

Authors
VANKLAVEREN M PERSSON ESM GROVE DM BACKVALL JE VANKOTEN G
Citation
M. Vanklaveren et al., THE USE OF ORTHO-CHELATING ARENETHIOLATE NONTRANSFERABLE GROUPS IN THE COPPER(I) CATALYZED SELECTIVE ALPHA-SUBSTITUTION OR GAMMA-SUBSTITUTION OF ACYCLIC ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS, Tetrahedron letters, 35(32), 1994, pp. 5931-5934
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
32
Year of publication
1994
Pages
5931 - 5934
Database
ISI
SICI code
0040-4039(1994)35:32<5931:TUOOAN>2.0.ZU;2-#
Abstract
Ortho-amino arenethiolatocopper(I) compounds are excellent catalysts f or the cross-coupling reaction of Grignard reagents with acyclic allyl ic substrates. For example, reaction of n-BuMgI with geranyl acetate i n Et(2)O at 0 degrees C yields quantitatively the gamma substitution p roduct, whereas the same reaction in THF at -30 degrees C affords sele ctively the a substitution product.