The silyl-cupration and stannyl-cupration of allenes

doi:10.1016/0040-4020(89)80069-9

Tetrahedron

Volume 45, Issue 2, 1989, Pages 413-424

https://doi.org/10.1016/0040-4020(89)80069-9 Get rights and content

Abstract

The stoichiometric silyl-cupration of allene 7, followed directly by treating the intermediate cuprate with a proton, with a range of carbon electrophiles, and with chlorine gives the vinylsilanes 8–13. Alternatively, when iodine is the electrophile, the product is the vinyl iodide 16. This can then be metallated and treated with a proton or a range of

carbon electrophiles to give the allylsilanes 18–21. More-substituted allenes also undergo silyl-cupration followed by protonation, phenylallenes giving vinylsilanes, and alkylallenes giving, on the whole, allylsilanes. Stoichiometric stannyl-cupration of allenes takes place, with similar but less reliable regiocontrol to that of the corresponding silyl-cupration.

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The silyl-cupration and stannyl-cupration of allenes

Abstract

Tetrahedron Lett.

J. Chem. Soc. Chem. Commun.

Canad. J. Chem.

Organometallics

Synthesis

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Israel J. Chem.

J. Org. Chem.

J. Am. Chem. Soc.

Chem. Ber.

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Tetrahedron Lett.

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Aust. J. Chem.

J. Organomet. Chem.

SnZn/Cu, SnAl/Cu, and SnMg/Cu

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J. Org. Chem.

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SnB/Cu

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SiB/Cu and SnB/Cu

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SiAl/Cu, SiZn/Cu, and SiMg/Cu

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SiSi/Mn and SnSn/Mn

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SiSi/Mn and SnSn/Mn

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SnSn/Pd

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SnSn/Pd

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SnSi/Pd

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J. Organomet. Chem.

SiSi/Pd

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SiSi/Pd

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