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Issue 9, 2014
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1,2-Migration in the reactions of ruthenium vinyl carbene with propargyl alcohols

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Abstract

Reactions of the ruthenium vinyl carbene complex [Ru{CHC(PPh3)CH(2-Py)}Cl2PPh3]BF4 (1) with five propargyl alcohols HC[triple bond, length as m-dash]CC(OH)R1R2, (R1 = R2 = Ph; R1 = Ph, R2 = CH3; R1 = H, R2 = Ph; R1 = H, R2 = CH3; R1 = CH[double bond, length as m-dash]CH2, R2 = CH3) have been investigated, which led to the formation of several ten-membered η2-olefin coordinated ruthenacycles [Ru{O[double bond, length as m-dash]CR2CHR12-CH[double bond, length as m-dash]CHC(PPh3)[double bond, length as m-dash]CH(2-Py)}Cl2PPh3]BF4 (R1 = R2 = Ph, 2; R1 = Ph, R2 = CH3, 3; R1 = H, R2 = Ph, 4; R1 = H, R2 = CH3, 5; R1 = CH[double bond, length as m-dash]CH2, R2 = CH3, 6), respectively. In these reactions, insertion of alkynes and intramolecular 1,2-migration of propargyl alcohols were performed in tandem. The results show that the 1,2-migratory preference of the groups is in the order of H > Ph > CH3. Complexes 2, 3, 5, and 6 were characterized by X-ray diffraction analysis and NMR spectra.

Graphical abstract: 1,2-Migration in the reactions of ruthenium vinyl carbene with propargyl alcohols

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Publication details

The article was received on 20 May 2014, accepted on 25 Aug 2014 and first published on 26 Aug 2014


Article type: Research Article
DOI: 10.1039/C4QO00152D
Org. Chem. Front., 2014,1, 1077-1082

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    1,2-Migration in the reactions of ruthenium vinyl carbene with propargyl alcohols

    X. Zhou, C. Zhang, Y. Lin, X. He, Y. Zhang, J. Wang and H. Xia, Org. Chem. Front., 2014, 1, 1077
    DOI: 10.1039/C4QO00152D

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