Organic Letters
Letter
of copper(II) acetate to regenerate the active rhodium(III)
Chem. Rev. 2020, 120 (4), 1981−2048. (j) Engle, K. M.; Mei, T.-S.;
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complex A for the next catalytic cycle. Intermediate E is
involved in the formation of branched alkene products.
In conclusion, we have demonstrated an aerobic oxidative
vinylic C−H alkenylation of acrylamides with unactivated
olefins catalyzed by a rhodium(III) complex that provides
amide-functionalized butadienes in good to moderate yields.
Various substituted acrylamides and functionalized unactivated
alkenes were compatible with the present catalytic reaction.
The alkenylation reaction was also demonstrated with Weinreb
amides. The catalytic cycle involving vinylic C−H activation
via a concerted metalation−deprotonation pathway and a five-
membered rhodacycle intermediate was illustrated.
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ASSOCIATED CONTENT
sı Supporting Information
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*
(
g) Reddy, M. C.; Jeganmohan, M. Chem. Commun. 2015, 51,
General experimental procedures and characterization
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0738−10741. (h) Parthasarathy, K.; Bolm, C. Chem. - Eur. J. 2014,
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13
details and H NMR and C NMR spectra of all
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Ravichandran Logeswaran − Department of Chemistry,
Indian Institute of Technology Madras, Chennai 600036,
Tamil Nadu, India
2
(
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Notes
Chem. Commun. 2016, 52, 10129−10132. (d) Manoharan, R.;
The authors declare no competing financial interest.
Sivakumar, G.; Jeganmohan, M. Chem. Commun. 2016, 52, 10533−
10536. (e) Dhawa, U.; Tian, C.; Li, W.; Ackermann, L. ACS Catal.
ACKNOWLEDGMENTS
2020, 10 (11), 6457−6462.
7) (a) Shang, X.; Liu, Z.-Q. Chem. Soc. Rev. 2013, 42, 3253. (b) Xu,
Y. H.; Lu, J.; Loh, T. P. J. Am. Chem. Soc. 2009, 131, 1372.
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(
We thank the DST-SERB (CRG/2018/000606), India for the
support of this research. R.L. thanks the CSIR for the
fellowship.
(c) Hatamoto, Y.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2004, 6, 4623.
(d) Bruneau, C.; Dixneuf, P. H. Top. Organomet. Chem. 2015, 55, 137.
(e) Liang, Q.-J.; Yang, C.; Meng, F.-F.; Jiang, B.; Xu, Y.-H.; Loh, T.-P.
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