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.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Shibata K,Natsui S,Tobisu M,Fukumoto Y,Chatani Ndoi
10.1038/s41467-017-01531-2subject
Has Abstractpub_date
2017-11-13 00:00:00pages
1448issue
1issn
2041-1723pii
10.1038/s41467-017-01531-2journal_volume
8pub_type
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