Palladium(0)-catalyzed cross-coupling of potassium (Z)-2-chloroalk-1-enyl trifluoroborates: a chemo- and stereoselective access to (Z)-chloroolefins and trisubstituted alkenes.
We describe the preparation of a series of new potassium trifluoroborates 1 and the study of their behaviour in a Pd(0)-catalyzed cross-coupling reaction. We found that compounds 1 are endowed with original properties as they behave as nucleophilic cross-coupling partners chemoselectively but also as ambivalent synthons. The usefulness of this methodology has been successfully illustrated by the first total synthesis of an N-acyl spermidine.
Guinchard
Xavier
X
CNRS-Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Bugaut
Xavier
X
Cook
Cyril
C
Roulland
Emmanuel
E
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*; D013095:Spermidine / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D001881:Borates; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D010165:Palladium; D011188:Potassium; D013095:Spermidine