Synthesis of new imines and amines containing organosilicon groups

The Peterson olefination reaction of terephthalaldehyde with tris(trimethylsilyl)methyl lithium, (Me3Si)3CLi, in THF at 0 °C gives 4-[2,2-bis(trimethylsilyl)ethenyl]benzaldehyde (1) and 4,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene (2). The new aldehyde (1) reacts with variety of amines in ethanol to afford the corresponding imines (3) containing vinylbis(trimethylsilyl) group. The newly synthesized imines (3) can be completely converted into amines containing vinylbis(trimethylsilyl) group with an excess amount of NaBH4. In the case of N-[4-(2,2-bis(trimethylsilyl)ethenyl)benzyl]-2,6-dimethylaniline LiAlH4 was used as a reducing agent in THF.

The Peterson olefination reaction of terephthalaldehyde with (Me3Si)3CLi, in THF at 0 °C gives 4-[2,2-bis(trimethylsilyl)ethenyl]benzaldehyde (1). The new aldehyde (1) reacts with variety of amines in ethanol to afford the corresponding imines (3). The newly synthesized imines (3) can be completely converted into amines containing vinylbis(trimethylsilyl) group with an excess amount of NaBH4.Figure optionsDownload as PowerPoint slideResearch highlights
► The newly synthesized imines and amines containing vinylbis(trimethylsilyl) group.
► The convenient one-pot preparation of 4-[2,2-bis(trimethylsilyl)ethenyl]benzaldehyde (1) via Peterson protocol.
► These imines might be used as intermediate for the synthesis of attractive molecules containing organosilicon group.
► The reaction of imines containing organosilicon groups with NaBH4 gives the corresponding secondary amines containing organosilicon groups.