Organic Letters
Letter
(
3) For recent examples of Pd-, Cu-, and Fe-catalyzed cross-couplings
on alkyl electrophiles, see: (a) He, A.; Falck, J. R. J. Am. Chem. Soc.
010, 132, 2524. (b) Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.;
dihaloalkanes that generates cyclopropane and cyclohexane, see:
(b) Vanalabhpatana, P.; Peters, D. G. J. Electrochem. Soc. 2005, 152,
E222. (c) Dahm, C. E.; Peters, D. G. J. Electrochem. Chem. 1996, 406,
119.
2
Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086. (c) Hatakeyama, T.;
Hashimoto, T.; Kondo, Y.; Fujiwara, Y.; Seike, H.; Takaya, H.;
Tamada, Y.; Ono, T.; Nakamura, M. J. Am. Chem. Soc. 2010, 132,
(16) For mechanistic studies that implicate NiI and NiIII
intermediates in Ni-catalyzed Negishi reactions, see: (a) Jones, G.
D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.;
Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A.
J. Am. Chem. Soc. 2006, 128, 13175. (b) Lin, X.; Phillips, D. L. J. Org.
1
̈
0674. (d) Furstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard,
R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773. (e) Hu, X.;
Cheung, C.; Ren, P. Org. Lett. 2014, 16, 2566.
(
a) Binder, J. T.; Cordier, C. J.; Fu, G. C. J. Am. Chem. Soc. 2012, 134,
4) For examples of Ni-catalyzed alkyl−alkyl Negishi reactions, see:
Chem. 2008, 73, 3680. (c) Phapale, V. B.; Bun
̃
uel, E.; García-Iglesias,
(
M.; Cardenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790.
́
1
2
1
1
1
7
7003−17006. (b) Son, S.; Fu, G. C. J. Am. Chem. Soc. 2008, 130,
756−2757. (c) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127,
0482−10483. (d) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125,
(17) (a) Breitenfeld, J.; Ruiz, J.; Wodrich, M. D.; Hu, X. J. Am. Chem.
Soc. 2013, 135, 12004. (b) Biswas, S.; Weix, D. J. J. Am. Chem. Soc.
2013, 135, 16192.
́
4726. (e) Gong, H.; Sinisi, R.; Gagne, M. R. J. Am. Chem. Soc. 2007,
29, 1908−1909. (f) Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67,
9−85.
(
5) For examples of Ni-catalyzed alkyl−alkyl Kumada reactions, see:
(
a) Breitenfeld, J.; Ruiz, J.; Wodrich, M. D.; Hu, X. J. Am. Chem. Soc.
2
013, 135, 12004. (b) Garcia, P. M. P.; Di Franco, T.; Orsino, A.; Ren,
P.; Hu, X. Org. Lett. 2012, 14, 4286. (c) Vechorkin, O.; Hu, X. Angew.
Chem., Int. Ed. 2009, 48, 2937. (d) Ren, P.; Vechorkin, O.; von
Allmen, K.; Scopelliti, R.; Hu, X. L. J. Am. Chem. Soc. 2011, 133, 7084.
(
e) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am.
Chem. Soc. 2002, 124, 4222.
6) For examples of Ni-catalyzed alkyl−alkyl Suzuki reactions, see:
a) Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem.
Soc. 2012, 134, 5794. (b) Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc.
(
(
2
2
011, 133, 15362. (c) Lu, Z.; Wilsily, A.; Fu, G. C. J. Am. Chem. Soc.
011, 133, 8154. (d) Nathan, A.; Owston, N. A.; Fu, G. C. J. Am.
Chem. Soc. 2010, 132, 11908. (e) Lu, Z.; Fu, G. C. Angew. Chem., Int.
Ed. 2010, 49, 6676.
(
7) For Ni-catalyzed Heck and related reactions, see: (a) Liu, C.;
Tang, S.; Liu, D.; Yuan, J.; Zheng, L.; Meng, L.; Lei, A. Angew. Chem.,
Int. Ed. 2012, 51, 3638. (b) Matsubara, R.; Gutierrez, A. C.; Jamison,
T. F. J. Am. Chem. Soc. 2011, 133, 19020. (c) Liu, C.; Liu, D.; Zhang,
W.; Zhou, L. L.; Lei, A. W. Org. Lett. 2013, 15, 6166. (d) Tang, S.; Liu,
C.; Lei, A. W. Chem. Commun. 2013, 49, 2442.
(
8) For recent reviews on reductive coupling of two electrophiles,
see: (a) Knappke, C. E. I.; Grupe, S.; Gartner, D.; Corpet, M.;
̈
Gosmini, C.; von Wangelin, A. J. Chem.Eur. J. 2014, 20, 6828.
(
(
b) Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 80, 4793.
c) Moragas, T.; Correa, A.; Martin, R. Chem.Eur. J. 2014, 20, 8242.
(
9) (a) Goldup, S. M.; Leigh, D. A.; McBurney, R. T.; McGonigal, P.
R.; Plant, A. Chem. Sci. 2010, 1, 383. (b) Prinsell, M. R.; Everson, D.
A.; Weix, D. J. Chem. Commun. 2010, 46, 5743. (c) Peng, Y.; Luo, L.;
Yan, S.; Zhang, J.; Wang, Ya. J. Org. Chem. 2013, 78, 10960. (d) Iyoda,
M.; Sakaitan, M.; Otsuka, H.; Oda, M. Chem. Lett. 1985, 14, 127.
(
2
(
2
10) Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13,
138.
11) Xu, H.; Zhao, C.; Qian, Q.; Deng, W.; Gong, H. Chem. Sci.
013, 4, 4022.
12) (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111,
(
1
780−1824. (b) Lei, A.; Zhang, X. Org. Lett. 2002, 4, 2285. (c) Li, C.-
J. Acc. Chem. Res. 2009, 42, 335. (d) Shi, W.; Liu, C.; Lei, A. Chem. Soc.
Rev. 2011, 40, 2761.
(
13) Zn: (a) Shortridgre, R. W.; Craigk, A.; Greenleej, W.; Derfer,
M.; Boord, C. E. J. Am. Chem. Soc. 1948, 70, 946. Cr(II): (b) Kochi, J.;
Singleton, D. J. Org. Chem. 1968, 33, 1027. Co: (c) Chock, P. B.;
Halpern, J. J. Am. Chem. Soc. 1969, 91, 582. Alkali naphthalenes:
(
(
d) Garst, J. F.; Barbas, J. T. J. Am. Chem. Soc. 1974, 96, 3239. t-BuLi:
e) Bailey, W. F.; Gagnier, R. P.; Patricia, J. J. J. Org. Chem. 1984, 49,
2
(
098−2107.
14) For activated Cu-mediated cyclization of α,ω-dihaloalkanes, see:
Ginah, F. O.; Donovan, T. A.; Suchuan, S. D.; Pfenning, D. R.; Ebert,
G. W. J. Org. Chem. 1990, 55, 584.
(
15) For a stoichiometric Ni(I) macrocycle-mediated cyclization of
,5-dihaloalkanes, see: (a) Ram, M. S.; Bakac, A.; Espenson, J. H. Inorg.
Chem. 1988, 27, 4231. For Ni-catalyzed electrochemical reduction of
1
4
987
dx.doi.org/10.1021/ol502207z | Org. Lett. 2014, 16, 4984−4987