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Journal of the American Chemical Society
Corresponding Author
(7) For a recent review of metal-catalyzed Csp3–Csp3 coupling, see:
Choi, J.; Fu, G. C. Transition metal–catalyzed alkyl-alkyl bond for-
mation: Another dimension in cross-coupling chemistry. Science 2017,
356, eaaf7230.
1
2
3
4
*dmacmill@princeton.edu
*rincon_juan_antonio@lilly.com
Author Contributions
(8) Although slower to develop than their aromatic counterparts
(vide infra), as well as traditional cross-coupling methodologies, there
§
R.T.S. and X.Z. contributed equally.
3
have been reports of Csp3–Csp cross-electrophile coupling. For exam-
5
ples, see: (a) Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Nickel-
Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides.
Org. Lett. 2011, 13, 2138. (b) Xu, H.; Zhao, C.; Qian, Q.; Deng, W.;
Gong, H. Nickel-catalyzed cross-coupling of unactivated alkyl halides
using bis(pinacolato)diboron as reductant. Chem. Sci. 2013, 4, 4022.
(c) Liang, Z.; Xue, W.; Lin, K.; Gong, H. Nickel-Catalyzed Reductive
Methylation of Alkyl Halides and Acid Chlorides with Methyl p-To-
sylate. Org. Lett., 2014, 16, 5620. (d) Liu, J.-H.; Yang, C.-T.; Lu, X.-
Y.; Zhang, Z.-Q.; Xu, L.; Cui, M.; Lu, X.; Xiao, B.; Fu, Y.; Liu, L.
Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl
Tosylates and Mesylates with Alkyl and Aryl Bromides. Chem.–Eur.
J. 2014, 20, 15334. (e) For an example of a reductive dimerization of
alkyl electrophiles, see: Prinsell, M. R.; Everson, D. A.; Weix, D. J.
Nickel-catalyzed, sodium iodide-promoted reductive dimerization of
alkyl halides, alkyl pseudohalides, and allylic acetates. Chem. Com-
mun. 2010, 46, 5743.
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Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
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Financial support provided by the NIHGMS (R01
GM093213) and kind gifts from Merck, BMS, Janssen, and
Eli Lilly. This work was supported by Eli Lilly and Company
through the Lilly Research Award Program (LRAP).
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