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
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作者:
VANKLAVEREN, M
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机构:UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
VANKLAVEREN, M
PERSSON, ESM
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机构:UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
PERSSON, ESM
GROVE, DM
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机构:UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
GROVE, DM
BACKVALL, JE
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机构:UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
BACKVALL, JE
VANKOTEN, G
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机构:UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
VANKOTEN, G
机构:
[1] UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
[2] UNIV UTRECHT,DEBYE RES INST,DEPT MET MEDIATED SYNTH,3584 CH UTRECHT,NETHERLANDS
Ortho-amino arenethiolatocopper(I) compounds are excellent catalysts for the cross-coupling reaction of Grignard reagents with acyclic allylic substrates. For example, reaction of n-BuMgI with geranyl acetate in Et(2)O at 0 degrees C yields quantitatively the gamma substitution product, whereas the same reaction in THF at -30 degrees C affords selectively the a substitution product.