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Journal of the American Chemical Society
ASSOCIATED CONTENT
Supporting Information
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General experimental procedures, kinetic data, characterization
data, spectral data, computational files, and optical spectroscopy
equipment/procedures. The Supporting Information is available
free of charge on the ACS Publications website.
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2012, 134, 4026-4029. b) Liu, W; Huang, X.; Cheng, M.; Niel-
son, R. J.; Goddard III, W. A.; Groves, J. T. Science 2012, 337,
1322-1325. c) Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc.
2012, 134, 10401-10404. d) Liu, W.; Groves, J. T. Angew. Chem.
Int. Ed. 2013, 52, 6024-6027. e) Amaoka, Y.; Nagamoto, M.;
Inoue, M. Org Lett. 2013, 15, 2160-2163. f) Braun, M-G.; Doyle,
A. J. Am. Chem. Soc. 2013, 135, 12990-12993. g) Xia, J-B.; Ma,
Y.; Chen, C. Org. Chem. Front. 2014, 1, 468-472. h) Rueda-
Becerril, M.; Mahe, O.; Drouin, M.; Majewski, M. B.; West, J. G.;
Wolf, M. O.; Sammis, G. M.; Paquin, J-F. J. Am. Chem. Soc.
2014, 136, 2637-2641. i) Halperin, S. D.; Fan, H.; Chang, S.;
Martin, R. E.; Britton, R. Angew. Chem. Int. Ed. 2014, 53, 4690-
4693. j) Li, Z.; Wang, Z.; Zhu, L.; Tan, X.; Li, C. J. Am. Chem.
Soc. 2014, 136, 16439-16443. k) Phae-nok, S.; Soorukram, D.;
Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. Eur. J. Org. Chem.
2015, 2015, 2879-2888. l) Ventre, S.; Petronijevic, F. P.; Mac-
Millan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654-5657.
AUTHOR INFORMATION
Corresponding Authors
*lectka@jhu.edu, artbragg@jhu.edu
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ACKNOWLEDGMENT
T. L. would like to thank the National Science Foundation (NSF)
(CHE-1465131) for support. A.E.B gratefully acknowledges
support from National Science Foundation (NSF) (CHE-
1455009).
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Adapted from: Lorenz, J. C.; Long, J.; Yang, Z.; Xue, S.; Xie,
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Fluorine has been referred to as the "second-favorite heteroa-
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For some recent literature, see: a) Böhm, H-J.; Banner, D.;
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Chen, G.; Song, J.; Yu, Y.; Luo, X.; Li, C.; Huang, X. Chem.
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Sci. 2016, 7, 1786-1790.
Good correlation is also noted with σ values, with no change
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in slope (Selectfluor, ρ = -3.2, R2 = 0.98; NFSI, ρ = -3.6, R2 =
0.97).
19
Electrophilic aromatic substitutions, for instance, tend to have
more negative ρ values attributed to formally cationic Wheland
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to, Y. J. Am. Chem. Soc. 1957, 79, 1913-1917. b) Johnson, C. D.
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Pitts, C. R.; Bloom, S.; Woltornist, R.; Auvenshine, D. J.;
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We have found that Hammett analyses for reactions with car-
6
Patel; N. R.; Flowers II, R. A. J. Org. Chem. 2015, 80, 5834-
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Dinnocenzo, J. P.; Zuilhof, H.; Lieberman, D. R.; Simpson, T.
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For some examples from our laboratory, see: a) Bloom, S.;
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Lectka, T. Angew. Chem. Int. Ed. 2012, 51, 10580-10583. b)
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Lectka, T. Org. Lett. 2013, 15, 1722-1724. c) Bloom, S.; Sharber,
S. A.; Holl, M. G.; Knippel, J. L.; Lectka, T. J. Org. Chem. 2013,
78, 11082-11086. d) Bloom, S.; Knippel, J. L.; Lectka, T. Chem.
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Org. Lett. 2014, 16, 6338-6341. f) Bloom, S.; Bume, D. D.; Pitts,
C. R.; Lectka, T. Chem. Eur. J. 2015, 21, 8060-8063.
21 For examples: a) Nicholas, A. M. de P.; Boyd, R. J.; Arnold, D.
R. Can. J. Chem. 1982, 60, 3011-3018. b) Wayner, D. D. M.;
Boyd, R. J.; Arnold, D. R. Can. J. Chem. 1983, 61, 2310-2315. c)
Wayner, D. D. M.; Boyd, R. J.; Arnold, D. R. Can. J. Chem.
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For other recent advances in this research area, see: a) Rueda-
Becerril, M.; Sazepin, C. C.; Leung, J. C. T.; Okbinoglu, T.;
Kennepohl, P.; Paquin, J-F.; Sammis, G. M. J. Am. Chem. Soc.
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CIDNP and EPR have been utilized, for examples: a) Roth, H.
D.; Herbertz, T.; Lakkaraju, P. S.; Sluggett, G.; Turro, N. J. J.
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