Organic Letters
Letter
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In conclusion, we have disclosed the first examples of
heteroannulations involving functionalization of a C(sp2)−H
bond in cyclobutene derivatives. These reactions offer an
efficient access to cylobutapyridones, and cyclobutapyridines
after post-functionalization, with unique substitution patterns
that cannot be attained using the classical photochemical
synthetic approach. These results pave the way for the
development of other transition-metal-catalyzed reactions
relying on the C−H bond activation of cyclobutenes.
2012, 51, 9372−9376. (e) Quin
ones, N.; Seoane, A.; García-Fandino,
̃ ̃
R.; Mascarenas, J. L.; Gulías, M. Chem. Sci. 2013, 4, 2874−2879.
̃
ASSOCIATED CONTENT
* Supporting Information
(f) Krieger, J.-P.; Lesuisse, D.; Ricci, G.; Perrin, M.-A.; Meyer, C.;
Cossy, J. Org. Lett. 2017, 19, 2706−2709. (g) Song, L.; Tian, G.; Van
der Eycken, J.; Van der Eycken, E. V. Beilstein J. Org. Chem. 2019, 15,
571−576.
■
S
The Supporting Information is available free of charge on the
(5) With a Ru catalyst, see: (a) Ackermann, L.; Lygin, A. V.;
Hofmann, N. Org. Lett. 2011, 13, 3278−3281. (b) Tulichala, R. N. P.;
Shankar, M.; Swamy, K. C. K. J. Org. Chem. 2017, 82, 5068−5079.
(c) Garad, D. N.; Mhaske, S. B. J. Org. Chem. 2019, 84, 1863−1870.
With a Co catalyst, see: (d) Grigorjeva, L.; Daugulis, O. Angew. Chem.,
Int. Ed. 2014, 53, 10209−10212. (e) Lerchen, A.; Knecht, T.; Koy,
M.; Daniliuc, C. G.; Glorius, F. Chem. - Eur. J. 2017, 23, 12149−
12152. With a Pd catalyst, see: (f) Yu, Y.; Huang, L.; Wu, W.; Jiang,
H. Org. Lett. 2014, 16, 2146−2149. With a Fe catalyst, see:
(g) Matsubara, T.; Ilies, L.; Nakamura, E. Chem. - Asian J. 2016, 11,
380−384.
Experimental procedures, characterization data, and
spectra for all new compounds (PDF)
AUTHOR INFORMATION
Corresponding Authors
■
ORCID
(6) (a) Wang, K.; Hu, F.; Zhang, Y.; Wang, J. Sci. China: Chem.
2015, 58, 1252−1265. (b) Shankar, M.; Guntreddi, T.; Ramesh, E.;
Sahoo, A. K. Org. Lett. 2017, 19, 5665−5668. See also references
cited therein.
Notes
(7) For the activation of C(sp3)−H bonds in cyclobutanes, see:
(a) Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133,
19076−19079. (b) He, J.; Shao, Q.; Wu, Q.; Yu, J.-Q. J. Am. Chem.
Soc. 2017, 139, 3344−3347. (c) Virelli, M.; Wang, W.; Kuniyil, R.;
Wu, J.; Zanoni, G.; Fernandez, A.; Scott, J.; Vendrell, M.; Ackermann,
L. Chem. - Eur. J. 2019, 25, 12712. See also references cited therein.
(8) Some cyclobuten-1-yl carboxylates undergo electrocyclic ring-
opening at 80−100 °C; for examples, see: (a) Jung, M. E.; Halweg, K.
The authors declare no competing financial interest.
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