Concepedia

One-pot synthetic route to homoallylketones via selective combination of alkyne, ethylene and aldehyde mediated by AlCl3 and zirconoceneElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b1/b109761j/

Changjia Zhao, Tao Yu, Zhenfeng Xi

Chemical Communications · 2002 · 31 citations · 11 references

DOI

Concepts

Abstract

Zirconacyclopentenes generated in situ from alkynes and ethylene undergo selective reaction with aldehydes to afford homoallylketones in yields exceeding 70% in the presence of AlCl3.

References

11

Facile cleavage of the CβCβ′ bond of zirconacyclopentenes. Convenient method for selectively coupling alkynes with alkynes, nitriles, and aldehydes

Tamotsu Takahashi, Motohiro Kageyama, Ryuichiro Hara et al. · Tetrahedron Letters · 1993 · 169 citations

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Multiple Mechanistic Pathways for Zirconium-Catalyzed Carboalumination of Alkynes. Requirements for Cyclic Carbometalation Processes Involving C−H Activation

Ei‐ichi Negishi, Denis Y. Kondakov, Danièle Choueiry et al. · Journal of the American Chemical Society · 1996 · 160 citations

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Carbon–Carbon Bond Cleavage and Selective Transformation of Zirconacycles

Tamotsu Takahashi, Martin Kotora, Ryuichiro Hara et al. · Bulletin of the Chemical Society of Japan · 1999 · 116 citations

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Highly Selective and Practical Alkyne-Alkyne Cross-Coupling Using Cp2ZrBu2 and Ethylene

Zhenfeng Xi, Ryuichiro Hara, Tamotsu Takahashi · The Journal of Organic Chemistry · 1995 · 115 citations

, , +7

Selective Intermolecular Coupling of Alkynes with Nitriles and Ketones via β,β‘ Carbon−Carbon Bond Cleavage of Zirconacyclopentenes

Tamotsu Takahashi, Chanjuan Xi, Zhenfeng Xi et al. · The Journal of Organic Chemistry · 1998 · 91 citations

, , +14