Organic Letters
Letter
2016, 116, 10075. (g) Goddard, J.-P.; Ollivier, C.; Fensterbank, L.
Acc. Chem. Res. 2016, 49, 1924.
(9) (a) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116,
10035. (b) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.;
MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 0052. (c) Cavalcanti, L.
N.; Molander, G. A. Top. Curr. Chem. 2016, 374, 39.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
(10) Selected examples: (a) Zuo, Z.; Ahneman, D. T.; Chu, L.;
Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345,
437. (b) Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem.
Soc. 2015, 137, 624. (c) Johnston, C. P.; Smith, R. T.; Allmendinger,
S.; MacMillan, D. W. C. Nature 2016, 536, 322. (d) Zuo, Z.; Cong,
H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. C. J. Am. Chem. Soc.
2016, 138, 1832. (e) Fan, L.; Jia, J.; Hou, H.; Lefebvre, Q.; Rueping,
M. Chem. - Eur. J. 2016, 22, 16437.
(11) Selected examples: (a) Tellis, J. C.; Primer, D. N.; Molander, G.
A. Science 2014, 345, 433. (b) Alam, R.; Molander, G. A. J. Org. Chem.
2017, 82, 13728. (c) Primer, D. N.; Molander, G. A. J. Am. Chem. Soc.
2017, 139, 9847. (d) Amani, J.; Sodagar, E.; Molander, G. A. Org.
Lett. 2016, 18, 732.
General procedures, characterization of products,
physical studies, copies of NMR spectra, and SFC traces
AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
(12) Selected examples: (a) Nakajima, K.; Nojima, S.; Nishibayashi,
́
Y. Angew. Chem., Int. Ed. 2016, 55, 14106. (b) Gutierrez-Bonet, A.;
Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal.
2016, 6, 8004. (c) Buzzetti, L.; Prieto, A.; Roy, S. R.; Melchiorre, P.
Angew. Chem., Int. Ed. 2017, 56, 15039.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(13) Selected examples: (a) Shaw, M. H.; Shurtleff, V. W.; Terrett, J.
A.; Cuthbertson, J. D.; MacMillan, D. W. C. Science 2016, 352, 1304.
(b) Shields, B.; Doyle, A. G. J. Am. Chem. Soc. 2016, 138, 12719.
(c) Le, C.; Liang, Y.; Evans, R. W.; Li, X.; MacMillan, D. W. C. Nature
2017, 547, 79. (d) Perry, I. B.; Brewer, T. F.; Sarver, P. J.; Schultz, D.
M.; DiRocco, D. A.; MacMillan, D. W. C. Nature 2018, 560, 70.
(e) Shen, Y.; Gu, Y.; Martin, R. J. Am. Chem. Soc. 2018, 140, 12200.
(f) Heitz, D. R.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2016,
138, 12715.
We thank Victor Kronig, Thomas Mahoney, and Colin Dewar
(Dr. Reddy’s Laboratories) and Oliwia Matuszewska (Cardiff
University) for important analytical support. C.P. thanks
H2020-MSCA-ITN-2016 (722591 − PHOTOTRAIN) for a
predoctoral fellowship.
REFERENCES
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(21) We found that the imidazole ring might interfere with
reactivity. The reaction of 1a with 4-bromobenzonitrile in the
presence of 1 equiv of 1-methylimidazole affords 2a in a reduced 60%
yield.
(22) Comparing our enantioselective method to the standard
racemic procedure (using Ir(dF(CF3)2ppy)2(dtbbpy)PF6 as the
photocatalyst and dtbbpy as the ligand for Ni), the former is shown
to afford higher yields of a single major enantiomer for a selected
range of substrates.
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