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2005
Pyridine derivatives
R 0380
Palladium-Catalyzed α-Arylation of N-Protected 2-Piperidinones. — The zinc
of N-protected piperidinones (I), generated by treatment of the piperidinones
05- 126 enolates
with either LiN(Tms)2 or sBuLi followed by addition of ZnCl2, are arylated by aryl bromides in the presence of catalytic amounts of Pd(dba)2 and bulky electron-rich ligand
BPP to afford the corresponding α-arylated products in high yields. The employment
of zinc enolates as well as the nature of the base are found to be essential for the success
of the method. For benzyl derivative (Ia), sBuLi gives higher yields than by use of
LiN(Tms)2, in general. — (DE FILIPPIS, A.; GOMEZ PARDO, D.; COSSY*, J.;
Tetrahedron 60 (2004) 43, 9757-9767; Lab. Chim. Org., CNRS, Ec. Super. Phys.
Chim. Ind., F-75231 Paris, Fr.; Eng.) — Klein
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