Palladium(0)‐Catalyzed Cross‐Coupling of Potassium (Z)‐2‐Chloroalk‐1‐enyl Trifluoroborates: A Chemo‐ and Stereoselective Access to (Z)‐Chloroolefins and Trisubstituted Alkenes

Original and ambivalent: We describe the preparation of a series of new potassium trifluoroborates 1, and the study of their behaviour in a Pd0‐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. magnified image We describe the preparation of a series of new potassium trifluoroborates 1 and the study of their behaviour in a Pd0‐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.