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Issue 7, 2013
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Pd-catalysed reactions of alkynes with model distannanes and poly[di-(n-butyl)]stannane

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Abstract

A reinvestigation of Pd-catalysed alkyne (R′–C[triple bond, length as m-dash]CH; R′ = H, Ph) insertion chemistry involving R3SnSnR3 (3a: R = Me; 3b: R = n-Bu) was undertaken. Model distannyl ethylenes 4a–b (Me3SnCH[double bond, length as m-dash]CR′SnMe3) and 5a–b ((n-Bu)3SnCH[double bond, length as m-dash]CR′Sn(n-Bu)3) were reproduced and further characterized by NMR (119Sn, 13C, 1H) and UV-Vis spectroscopy. In the presence of an excess of phenylacetylene, dimerization–carbostannylation of compound 4b yielded the new conjugated butadiene, (Z,Z)-1,4-bis(trimethylstannyl)-1,4-diphenyl-buta-1,3-diene (9). An X-ray structure determination of 9 reveals a symmetrical double-bond Z confirmation. Compound 9 was further characterized by NMR, UV-Vis spectroscopy, and MS. A DFT analysis of model compounds (4a–b, 5a–b, 9) and the experimental and theoretical λmax values from the UV-Vis spectra were also compared. Acetylene and phenylacetylene Pd-catalysed insertion into the backbone of poly[di-(n-butyl)]stannane 12 resulted in new, modest molecular weight, partially inserted alkene tin polymers (13a–b) that were also characterized by GPC, NMR, UV-Vis spectroscopy and elemental analysis.

Graphical abstract: Pd-catalysed reactions of alkynes with model distannanes and poly[di-(n-butyl)]stannane

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Publication details

The article was received on 02 Aug 2012, accepted on 15 Nov 2012 and first published on 19 Nov 2012


Article type: Paper
DOI: 10.1039/C2DT31999C
Citation: Dalton Trans., 2013,42, 2469-2476
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    Pd-catalysed reactions of alkynes with model distannanes and poly[di-(n-butyl)]stannane

    A. Khan, A. J. Lough, R. A. Gossage and D. A. Foucher, Dalton Trans., 2013, 42, 2469
    DOI: 10.1039/C2DT31999C

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