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- Title
Rhodium‐Catalyzed Alkylation of C−H Bonds in Aromatic Amides with Non‐activated 1‐Alkenes: The Possible Generation of Carbene Intermediates from Alkenes.
- Authors
Yamaguchi, Takuma; Natsui, Satoko; Shibata, Kaname; Yamazaki, Ken; Rej, Supriya; Ano, Yusuke; Chatani, Naoto
- Abstract
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.
- Subjects
ARAMID fibers; ALKYLATION; RHODIUM catalysts; ALKENES; CARBOXYLIC acids
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 28, p6915
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201901300