PMID: 11916415Mar 28, 2002Paper

Ligand-modulated stereo- and regioselective tandem addition reactions of rhenium-bound naphthalene

Journal of the American Chemical Society
Mark T ValahovicW Dean Harman

Abstract

A series of complexes of the form TpRe(CO)(L)(eta(2)-naphthalene) (Tp = hydridotris(pyrazolyl)borate) undergoes tandem electrophile/nucleophile addition reactions with a high degree of regiocontrol depending on the auxiliary ligand, L. When L = PMe(3), the reaction of the eta(2)-naphthalene complex with triflic acid followed by a silyl ketene acetal favors the 1,4-addition product, whereas when L = pyridine, N,N-dimethylaminopyridine, N-methylimidazole, or NH(3) the 1,2-addition product is favored. These reactions proceed with excellent stereocontrol: both electrophile (H(+), D(+)) and nucleophile (silyl ketene acetal) add anti to the face of metal coordination, and a single coordination diastereomer can be isolated for each reaction. One-electron oxidation of the Re complex affords the corresponding free dihydronaphthalene in good yield.

References

Jul 27, 2001·Journal of the American Chemical Society·B C BrooksW D Harman
Oct 25, 2001·The Journal of Organic Chemistry·Anthony J. Pearson, Alexander V. Gontcharov

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Citations

May 14, 2008·Journal of the American Chemical Society·Michael A ToddW Dean Harman
Mar 31, 2004·The Journal of Organic Chemistry·Fei DingW Dean Harman
Oct 25, 2017·Chemical Reviews·Benjamin K Liebov, W Dean Harman
Nov 7, 2019·Journal of the American Chemical Society·Justin H WildeW Dean Harman
Feb 14, 2004·The Journal of Organic Chemistry·F Christopher PiggeNigam P Rath
Oct 21, 2004·Journal of the American Chemical Society·Fei Ding, W Dean Harman
Jan 22, 2004·Journal of the American Chemical Society·Joseph M KeaneW Dean Harman
Feb 20, 2003·Journal of the American Chemical Society·Scott H MeiereW Dean Harman
Nov 26, 2004·Journal of the American Chemical Society·Philip L SmithW Dean Harman
May 27, 2004·Journal of the American Chemical Society·Joseph M KeaneW Dean Harman

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