Synthesis of 4-arylpiperidines from 1-benzyl-4-piperidone: application of the Shapiro reaction and alkenylsilane cross-coupling.
[reaction: see text] 1-Benzyl-3,4-unsaturated-4-piperidinyl benzyldimethylsilane has been prepared and observed to readily undergo palladium-catalyzed cross-coupling reactions with a variety of aryl iodides and aryl bromides to generate 3,4-unsaturated 4-arylpiperidines, often at ambient temperature.
Morrill
Christie
C
Department of Drug Discovery, Johnson & Johnson Pharmaceutical R&D LLC, 3210 Merryfield Row, San Diego, California 92121, USA. cmorril3@prdus.jnj.com
Mani
Neelakandha S
NS
D001593:Benzyl Compounds / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*; D010881:Piperidones / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
C520241:1-benzyl-4-piperidone; D001593:Benzyl Compounds; D001965:Bromides; D003432:Cross-Linking Reagents; D010880:Piperidines; D010881:Piperidones; D012821:Silanes