Catalytic Synthesis of n-Alkyl Arenes through Alkyl Group Cross-Metathesis
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Schrock_Catalytic synthesis with SI.pdf
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Author(s)
Dobereiner, Graham E.
Yuan, Jian
Schrock, Richard Royce
Goldman, Alan S.
Hackenberg, Jason D.
Date Issued
August 2013
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Dobereiner, Graham E., Jian Yuan, Richard R. Schrock, Alan S. Goldman, and Jason D. Hackenberg. “ Catalytic Synthesis of n -Alkyl Arenes through Alkyl Group Cross-Metathesis .” Journal of the American Chemical Society 135, no. 34 (August 28, 2013): 12572–12575.
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Author's final manuscript
Abstract
n-Alkyl arenes were prepared in a one-pot tandem dehydrogenation/olefin metathesis/hydrogenation sequence directly from alkanes and ethylbenzene. Excellent selectivity was observed when (tBuPCP)IrH[subscript 2] was paired with tungsten monoaryloxide pyrrolide complexes such as W(NAr)(C[subscript 3]H[subscript 6])(pyr)(OHIPT) (1a) [Ar = 2,6-i-Pr[subscript 2]C[subscript 6]H[subscript 3]; pyr = pyrrolide; OHIPT = 2,6-(2,4,6-i-Pr[subscript 3]C[subscript 6]H[subscript 2])[subscript 2]C[subscript 6]H[subscript 3]O]. Complex 1a was also especially active in n-octane self-metathesis, providing the highest product concentrations reported to date. The thermal stability of selected olefin metathesis catalysts allowed elevated temperatures and extended reaction times to be employed.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja4066392
