An unusual endo-selective C-H hydroarylationof norbornene by the Rh(I)-catalyzed reactionof benzamides

Kaname Shibata, Satoko Natsui, Mamoru Tobisu, Yoshiya Fukumoto and Naoto Chatani ()
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Kaname Shibata: Osaka University, Suita
Satoko Natsui: Osaka University, Suita
Mamoru Tobisu: Osaka University, Suita
Yoshiya Fukumoto: Osaka University, Suita
Naoto Chatani: Osaka University, Suita

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract Hydroarylation is an environmentally attractive strategy which incorporates all of the atoms contained in the substrates into the desired products. Almost all the hydroarylations of norbornene reported to date involve an exo-selective reaction. Here we show the endo-selective hydroarylation of norbornene in the Rh(I)-catalyzed reaction of aromatic amides. The addition of sterically bulky carboxylic acids enhances the endo-selectivity of the reaction. The results of deuterium-labeling experiments show that both the ortho-carbon and the ortho-hydrogen atoms of aromatic amides were attached to the same carbon atom of the norbornane skeleton in the hydroarylation product. These results clearly suggest that hydrometalation or carbometalation, which are commonly accepted mechanisms for the catalytic hydroarylation of C–H bonds, are not involved as the key step in the present reaction, and suggest that the reaction involves a rhodium carbene complex generated from norbornene as the key intermediate.

Date: 2017
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_s41467-017-01531-2

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DOI: 10.1038/s41467-017-01531-2

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