Organic Letters
Letter
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u) Kayahara, E.; Patel, V. K.; Yamago, S. J. Am. Chem. Soc. 2014, 136,
ASSOCIATED CONTENT
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284.
6) (a) Darzi, E. R.; Jasti, R. Chem. Soc. Rev. 2015, 44, 6401. (b) Golder,
M. R.; Jasti, R. Acc. Chem. Res. 2015, 48, 557.
7) (a) Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, T.; Yamago, S.
*
S
Supporting Information
(
(
Angew. Chem., Int. Ed. 2011, 50, 8342. (b) Iwamoto, T.; Watanabe, Y.;
Takaya, H.; Haino, T.; Yasuda, N.; Yamago, S. Chem. - Eur. J. 2013, 19,
Detailed experimental procedures; NMR spectra; crys-
computational details and coordinates (PDF)
1
4061. (c) Iwamoto, T.; Slanina, Z.; Mizorogi, N.; Guo, J.; Akasaka, T.;
Nagase, S.; Takaya, H.; Yasuda, N.; Kato, T.; Yamago, S. Chem. - Eur. J.
014, 20, 14403. (d) Ueno, H.; Nishihara, T.; Segawa, Y.; Itami, K.
2
Angew. Chem., Int. Ed. 2015, 54, 3707.
(8) Yoshizawa, M.; Klosterman, J. K. Chem. Soc. Rev. 2014, 43, 1885.
(9) Tasdelen, M. A. Polym. Chem. 2011, 2, 2133.
AUTHOR INFORMATION
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*
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1
10) (a) Li, M.; Schlu
34, 11721. (b) Kissel, P.; Erni, R.; Schweizer, W. B.; Rossell, M. D.;
King, B. T.; Bauer, T.; Gotzinger, S.; Schluter, A. D.; Sakamoto, J. Nat.
̈
ter, A. D.; Sakamoto, J. J. Am. Chem. Soc. 2012,
Notes
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Chem. 2012, 4, 287. (c) Bhola, R.; Payamyar, P.; Murray, D. J.; Kumar,
The authors declare no competing financial interest.
B.; Teator, A. J.; Schmidt, M. U.; Hammer, S. M.; Saha, A.; Sakamoto, J.;
̈
Schluter, A. D.; King, B. T. J. Am. Chem. Soc. 2013, 135, 14134. (d) Kory,
ACKNOWLEDGMENTS
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M. J.; Worle, M.; Weber, T.; Payamyar, P.; van de Poll, S. W.;
Financial support was provided by the National Science
Foundation (CH-1255219), the Sloan Foundation, the Camille
and Henry Dreyfus Foundation, and generous startup funds from
the University of Oregon. B.M.W. acknowledges the National
Science Foundation for the use of supercomputing resources
through the Extreme Science and Engineering Discovery
Environment (XSEDE), Project No. TG-CHE150040. The
authors would like to gratefully acknowledge Jonathan L.
Marshall (University of Oregon) for assistance with cyclic
voltammetry.
Dshemuchadse, J.; Trapp, N.; Schluter, A. D. Nat. Chem. 2014, 6, 779.
(
e) Murray, D. J.; Patterson, D. D.; Payamyar, P.; Bhola, R.; Song, W.;
Lackinger, M.; Schluter, A. D.; King, B. T. J. Am. Chem. Soc. 2015, 137,
450.
11) (a) Tobe, Y.; Takahashi, T.; Ishikawa, T.; Yoshimura, M.; Suwa,
M.; Kobiro, K.; Kakiuchi, K.; Gleiter, R. J. Am. Chem. Soc. 1990, 112,
889. (b) Tobe, Y.; Takahashi, T.; Kobiro, K.; Kakiuchi, K. J. Am. Chem.
̈
3
(
8
Soc. 1991, 113, 5804. (c) Tobe, Y.; Takemura, A.; Jimbo, M.; Takahashi,
T.; Kobiro, K.; Kakiuchi, K. J. Am. Chem. Soc. 1992, 114, 3479.
(12) Control experiments were conducted in which 1 or 2 was either
exposed to light in a deoxygenated atmosphere or stored under air in a
dark environment. Under either condition, 1 and 2 showed no evidence
of decomposition. Thus we conclude that the decomposition of 1 and 2
is likely a photochemical process that requires both light and oxygen.
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