The alkylation of C−H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C−H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.
|Number of pages||5|
|Journal||Chemistry - A European Journal|
|Publication status||Published - May 17 2019|
- C−H activation
- non-activated alkenes
ASJC Scopus subject areas
- Organic Chemistry