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.
Organic & Biomolecular Chemistry
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