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α-Selective Ni-Catalyzed Hydroalumination of Aryl- and Alkyl-Substituted Terminal Alkynes: Practical Syntheses of Internal Vinyl Aluminums, Halides, or Boronates

Fang Gao and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: amir.hoveydabc.edu

F. Gao, A. H. Hoveyda, J. Am. Chem. Soc., 2010, 132, 10961-10963.

DOI: 10.1021/ja104896b (free Supporting Information)


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Abstract

Reliable, operationally simple, catalytic α-selective hydroalumination reactions proceed in the presence of diisobutylaluminum hydride and (Ni(dppp)Cl2),  and, unlike uncatalyzed transformations, generate little or no alkynylaluminum byproducts. The derived α-vinyl halides and boronates can be synthesized through direct treatment with the appropriate electrophiles.

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Key Words

Vinyl bromides, Vinyl iodides, Vinylboronates, DIBAL-H, NBS, NIS


ID: J48-Y2010-2200