Platinum-catalysed 1,4-diboration of 1,3-dienes

William Clegg, Thorsten R.F. Johann, Todd B. Marder, Nicholas C. Norman, A. Guy Orpen, Torren M. Peakman, Michael J. Quayle, Craig R. Rice, Andrew J. Scott

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Abstract

The chiral diborane(4) compounds B2[R,R-O2CH(CO2Me)CH(CO2Me)] 2, B2(S,O2CH2CHPh)2, B2(R,R-O2-CHPhCHPh)2 and B2(O2C20H12)2 (O2C20H12 = 1,7′-bi-2-naphtholate) have been synthesized. All four compounds have been characterised by X-ray crystallography, the latter as a racemate. The B-B bond oxidativeaddition reactions of the first three compounds with [Pt(PPh3)2(μ-C2H4)] resulted in the platinum(II) bis(boryl) complexes cis-[Pt(PPh3)2{B[R,R-O2CH(CO 2Me)CH(CO2Me)]}2], cis-[Pt(PPh3)2{B(S-O2CH2CHPh)} 2] and cis-[Pt(PPh3)2{B(R,R-O2CHPhCHPh)}2]; the former two were also characterised by X-ray crystallography. The platinum-catalysed diborations of a range of prochiral 1,3-dienes with the compounds B2[R,R-O2CH(CO2Me)-CH(CO2Me)] 2, B2(S-O2CH2CHPh)2 and B2(R,R-O2CHPhCHPh)2 were studied. Although these reactions were clean and quantitative, observed product d.e.s (measured by 1H NMR spectroscopy) were low or non-existent indicating that chirality transfer from the diborane(4) diolate groups to the diene diboration product is not efficient in these cases.

Original languageEnglish
Pages (from-to)1431-1438
Number of pages8
JournalJournal of the Chemical Society - Dalton Transactions
Issue number9
DOIs
Publication statusPublished - 7 May 1998
Externally publishedYes

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Clegg, W., Johann, T. R. F., Marder, T. B., Norman, N. C., Orpen, A. G., Peakman, T. M., ... Scott, A. J. (1998). Platinum-catalysed 1,4-diboration of 1,3-dienes. Journal of the Chemical Society - Dalton Transactions, (9), 1431-1438. https://doi.org/10.1039/a800108a