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Palladium(0)‐Catalyzed Cross‐Coupling of Potassium ( Z )‐2‐Chloroalk‐1‐enyl Trifluoroborates: A Chemo‐ and Stereoselective Access to ( Z )‐Chloroolefins and Trisubstituted Alkenes
Author(s) -
Guinchard Xavier,
Bugaut Xavier,
Cook Cyril,
Roulland Emmanuel
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900425
Subject(s) - synthon , nucleophile , chemistry , coupling reaction , palladium , catalysis , potassium , coupling (piping) , stereoselectivity , stereochemistry , spermidine , medicinal chemistry , organic chemistry , combinatorial chemistry , materials science , enzyme , metallurgy
Original and ambivalent : 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.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.