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Issue 9, 2013
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Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

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Abstract

The functionalisation of decalin by means of an “aliphatic Friedel–Crafts” reaction was reported over fifty years ago by Baddeley et al. This protocol is of current relevance in the context of C–H activation and here we demonstrate its applicability to a range of other saturated hydrocarbons. Structural elucidation of the products is described and a mechanistic rationale for their formation is presented. The “aliphatic Friedel–Crafts” procedure allows for production of novel oxygenated building blocks from abundant hydrocarbons and as such can be considered to add significant synthetic value in a single step.

Graphical abstract: Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

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Supplementary files

Article information


Submitted
07 Sep 2012
Accepted
12 Dec 2012
First published
21 Dec 2012

Org. Biomol. Chem., 2013,11, 1468-1475
Article type
Paper

Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

C. L. Lyall, M. Uosis-Martin, J. P. Lowe, M. F. Mahon, G. D. Pantoş and S. E. Lewis, Org. Biomol. Chem., 2013, 11, 1468
DOI: 10.1039/C2OB26765A

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