Organic Letters
Letter
(9) (a) Mai, D. N.; Baxter, R. D. Org. Lett. 2016, 18, 3738−3741.
(b) Fujiwara, Y.; Dixon, J. A.; O’Hara, F.; Funder, E. D.; Dixon, D. D.;
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system to alkylate and arylate heteroarenes and quinones. Mild
reaction conditions yield high levels of monoselectivity for
heteroarene and quinone alkylations, and allow reactions with
sensitive radical precursors. Arylation of heteroarenes and
quinones is also effective from a variety of arylboronic acid
radical precursors. Ongoing work in this area involves
expanding the scope of substrates and radical precursors that
participate in C−H functionalization. In addition, mechanistic
work is underway to identify fundamental reactivity differences
between the traditional Minisci reaction and one involving
Selectfluor as an oxidant.
(10) For oxidation potentials of α-aminoalkyl radicals, see:
(a) Armstrong, D. A.; Rauk, A.; Yu, D. J. Am. Chem. Soc. 1993, 115,
666−673. For Minisci reactions from α-aminoalkyl radicals derived
from amino acids, see: (b) Cowden, C. J. Org. Lett. 2003, 5, 4497−
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photocatalyzed Minisci-type reactions involving sensitive α-amino- and
α-oxyalkyl radicals, see: (e) Zuo, Z.; MacMillan, D. W. C. J. Am. Chem.
Soc. 2014, 136, 5257−5260. (f) Jin, J.; MacMillan, D. W. C. Angew.
Chem., Int. Ed. 2015, 54, 1565−1569.
ASSOCIATED CONTENT
* Supporting Information
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S
(11) Gianatassio, R.; Kawamura, S.; Eprile, C. L.; Foo, K.; Ge, J.;
Burns, A. C.; Collins, M. R.; Baran, P. S. Angew. Chem., Int. Ed. 2014,
53, 9851−9855. (b) Matsui, J. K.; Primer, D. N.; Molander, G. A.
Chem. Sci. 2017, 8, 3512−3522.
The Supporting Information is available free of charge on the
(12) (a) Colucci, M. A.; Couch, G. D.; Moody, C. J. Org. Biomol.
Detailed experimental procedures, full characterization,
Chem. 2008, 6, 637−656. (b) Urgin, K.; Jida, M.; Ehrhardt, K.; Muller,
̈
T.; Lanzer, M.; Maes, L.; Elhabiri, M.; Davioud-Charvet, E. Molecules
2017, 22, 161. (c) Nasiri, H. R.; Madej, M. G.; Panisch, R.; Lafontaine,
M.; Bats, J. W.; Lancaster, C. R. D.; Schwalbe, H. J. Med. Chem. 2013,
56, 9530−9541.
AUTHOR INFORMATION
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Corresponding Author
ORCID
(13) (a) Khader, M.; Eckl, P. M. Iran J. Basic Med. Sci. 2014, 17,
950−957. (b) Worthen, D.; Ghosheh, O. A.; Crooks, P. Anticancer Res.
1998, 18, 1527−1532.
(14) (a) Fieser, L. F.; Oxford, A. E. J. Am. Chem. Soc. 1942, 64,
2060−2065. (b) Yamago, S.; Hashidume, M.; Yoshida, J-i. Chem. Lett.
2000, 29, 1234−1235. (c) Ngwira, K. J.; Rousseau, A. L.; Johnson, M.
M.; de Koning, C. B. Eur. J. Org. Chem. 2017, 2017, 1479−1488.
Notes
The authors declare no competing financial interest.
(d) Frohlich, T.; Ndreshkjana, B.; Muenzner, J. K.; Reiter, C.;
̈
Hofmeister, E.; Mederer, S.; Fatfat, M.; El-Baba, C.; Gali-Muhtasib, H.;
Schneider-Stock, R.; Tsogoeva, S. B. ChemMedChem 2017, 12, 226−
234. (e) Breyer, S.; Effenberger, K.; Schobert, R. ChemMedChem 2009,
ACKNOWLEDGMENTS
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Financial support for this work was provided by the University
of California, Merced. J.D.G. acknowledges the UCM MACES
Center for a graduate fellowship.
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4, 761−768. For a very recent example, see: (f) Gutierrez-Bonet, A.;
Remeur, C.; Matsui, J. K.; Molander, G. A. J. Am. Chem. Soc. 2017,
139, 12251−12258.
(15) Baxter, R. D.; Liang, Y.; Hong, X.; Brown, T. A.; Zare, R. N.;
Houk, K. N.; Baran, P. S.; Blackmond, D. G. ACS Cent. Sci. 2015, 1,
456−462.
REFERENCES
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