Journal of the American Chemical Society
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For example, Ni catalyzed C–O cross coupling is thermodynami-
and Biosciences, Office of Basic Energy Sciences of the U.S. De-
partment of Energy through Grant No. DE-SC0015429. We thank
Phil Jeffrey of Princeton University for X-ray crystallographic
structure determination.
17
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cally infeasible via Ni(II) reductive elimination (Figure 6). In
contrast, cross-coupling reactions which proceed via a Ni(III) in-
termediate are facile, suggesting that photoinduced disproportion-
ation could offer a mechanism for initiating Ni(I)/(III) catalytic cy-
cles for C–O cross coupling. In keeping with this hypothesis, a
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ASSOCIATED CONTENT
Supporting Information
13. Frei, F.; Rondi, A.; Espa, D.; Mercuri, M. L.; Pilia, L.; Serpe,
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AUTHOR INFORMATION
15. Brown, K. E.; Salamant, W. A.; Shoer, L. E.; Young, R. M.;
Corresponding Author
Wasielewski, M. R. J. Phys. Chem. Lett. 2014, 5, 2588.
16. Ishida, N.; Masuda, Y.; Ishikawa, N.; Murakami, M. Asian J.
Org. Chem. 2017, 6, 669.
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Notes
D. W. C. Nature 2015, 524, 330. (b) Welin, E. R.; Le, C.; Arias-
Rotondo, D. M.; McCusker, J. K.; MacMillan, D. W. C. Science
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The authors declare no competing financial interests.
ACKNOWLEDGMENTS
18. The efficiency of photocatalytic C–O coupling with Ni is
Financial support was provided by a Princeton Innovation Fund
grant and NIGMS (R01 GM100985) to AGD. GDS gratefully
acknowledges the Division of Chemical Sciences, Geosciences,
dependent on the reaction conditions (see SI), consistent with a
report by the MacMillan lab (ref 17a) wherein no background
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