10.1002/anie.201705521
Angewandte Chemie International Edition
COMMUNICATION
[1]
Coupling of tertiary R-MgX with 1o- and 2o-alkyl halides catalyzed by
Cu: a) J. Terao, H. Todo, S. A. Begum, H. Kuniyasu, N. Kambe, Angew.
Chem., Int. Ed. 2007, 46, 2086; b) P. Ren, L. A. Stern, X. L. Hu, Angew.
Chem., Int. Ed. 2012, 51, 9110; c) C.–T. Yang, Z.–Q. Zhang, J. Liang,
J.–H. Liu, X.–Y. Lu, H.–H. Chen, L. Liu, J. Am. Chem. Soc. 2012, 134,
11124; by Co: T. Iwasaki, H. Takagawa, S. P. Singh, H. Kuniyasu, N.
Kambe, J. Am. Chem. Soc. 2013, 135, 9604.
Coupling of styrenyl aziridines with organozincs to give all quaternary
carbon products, see: d) Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc.
2015, 137, 5638.
[9]
Catalytic C(sp3)−C(sp3) bond formation via cross-coupling of alkyl
electrophiles: a) H. Xu, C. Zhao, Q. Qian, W. Deng, H. Gong, Chem.
Sci. 2013, 4, 4022; b) X. Yu, T. Yang, S. Wang, H. Xu, H. Gong, Org.
Lett. 2011, 13, 2138. c) J.-H. Liu, C.-T. Yang, X.-Y. Lu, Z.-Q. Zhang, L.
Xu, M. Cui, X. Lu, B. Xiao, Y. Fu, L. Liu, Chem.–Eur. J. 2014, 20,
15334; d) E. J. Tollefson, L. W. Erickson, E. R. Jarvo, J. Am. Chem.
Soc. 2015, 137, 9760.
[2]
[3]
Coupling of teriary R-MgX with allylic electrophiles: a) A. M. Lauer, F.
Mahmud, .J. Wu, J. Am. Chem. Soc. 2011, 133, 9119–9123; b) X. Han,
Y. Zhang, J. Wu, J. Am. Chem. Soc. 2010, 132, 4104–4106; with
(tBu)2Zn: c) B. Breit, P. Demel, D. Grauer, C. Studte, Chem. Asian J.
2006, 1, 586–597.
[10] a) X. Qian, A. Auffrant, A. Felouat, C. Gosmini, Angew. Chem., Int. Ed.
2011, 50, 10402; In recent Pd-catalyzed electrochemical allylic
a
alkylation method, coupling of tBu-I with allyl bromide was disclosed as
a sole example for the formation of 4,4-dimethyl-1-pentene, albeit in low
yield, see: b) Y.-L.; J.-M. Huang, Org. Lett. 2017, 19, 2022. For more
examples of reductive allylation of primary and secondary alkyl halides,
see: a) Y. Dai, F. Wu, Z. Zang, H. You, H. Gong, Chem.‒Eur. J. 2012,
16, 808; b) L. L. Anka-Lufford, M. R. Prinsell, D. J. Weix J. Org. Chem.
2012, 77, 9989.
Coupling of tertiary alkyl halides with allylic and benzylic metallics: a) S.
K. Ghorai, M. Jin, T. Hatakeyama, M. Nakamura, Org. Lett. 2012, 14,
1066; b) H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett.
2008, 10, 969; c) Y. Mitamura, Y. Asada, K. Murakami, H. Someya, H.
Yorimitsu, K. Oshima, Chem. –Asian J. 2010, 5, 1487; d) T. Tsuji, H.
Yorimitsu, K. Oshima, Angew. Chem., Int. Ed. 2002, 41, 4137; e) H.
Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 2004, 10,
5640.
[11] Coupling of Ar-MgX with only adamantyl chloride is known: a) S. K.
Ghorai, M. Jin, T. Hatakeyama, M. Nakamura, Org. Lett. 2012, 14,
1066; b) Direct coupling of Ar2Zn with tertiary bromides including tBu-
and admantanyl-Br, see: J. J. Dunsford, R. Ewan, E. R.;Clark, M. J.
Ingleson, Angew. Chem., Int. Ed. 2015, 54, 5688.
[4]
[5]
α-Carbonyl allylation: a) G. Pupo, R. Properzi, B. List, Angew. Chem.,
Int. Ed. 2016, 55, 6099; b) M. Braun, T. Meier, Angew. Chem., Int. Ed.
2006, 45, 6952.
740; b) T. Matsuura, L. E. Overman, D. J. Poon, J. Am. Chem. Soc.
1998, 120, 6500; c) D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E.
White, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2012, 4, 130.
[12] For the coupling of adamantyl halides with CO2, see: a) M. Börjesson, T.
Moragas, R. Martin J. Am. Chem. Soc. 2016, 138, 7504-7507; b) E.
Serrano, R. Martin Angew. Chem. Int. Ed. 2016, 11207-11211
[13] See the Supplementary Information for details.
[6]
For reviews on reductive couplings, see: a) D. A. Everson, D. J. Weix, J.
Org. Chem. 2014, 79, 4793; b) J. Gu, Wang, X.; Xue, H. Gong, Org.
Chem. Front. 2015, 2, 1411; c) C. E. I. Knappke, S. Grupe, D. Gartner,
M. Corpet, C. Gosmini, J. A. von Wangelin, Chem.-Eur. J. 2014, 20,
6828; d) D. J. Weix, Acc. Chem. Res. 2015, 48, 1767; e) T. Moragas, A.
Correa, R. Martin, Chem.–Eur. J. 2014, 20, 8242; f) J. Y. Nédélec, J.
Perichon, M. Troupel, Top. Curr. Chem. 1997, 185, 141.
[14] a) R. González-Bobes, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 5360;
b) D. A. Powell, T. Maki, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 510;
c) X. Yu, T. Yang, S. Wang, H. Xu, H. Gong, Org. Lett. 2011, 13, 2138;
d) H. Xu, C. Zhao, Q. Qian, W. Deng, H. Gong, Chem. Sci. 2013, 4,
4022; e) S. E. Creutz, K. J. Lotito, G. C. Fu, J. C. Peters, Science 2012,
338, 647.
[15] For an example of carbonylation of η1-allyl–Ni, see: A. Bottoni, G. P.
[7]
[8]
a) C. Zhao, X. Jia, X. Wang, H. Gong, J. Am. Chem. Soc. 2014, 136,
17645; b) X. Wang, S. Wang, W. Xue, H. Gong, J. Am. Chem. Soc.
2015, 137, 11562.
Miscione, J. J. Novoa, X. Prat-Resina, J. Am. Chem. Soc. 2003, 125,
10412.
[16] For mechanistic studies involving allyl-Ni(I) and -Ni(II), see: a) L. S.
Hegedus, D. H. P. Thompson, J. Am. Chem. Soc. 1985, 107, 5663; b)
E. J. Corey, M. F. Semmelhack, L. S. Hegedus, J. Am. Chem. Soc.
1968, 90, 2416; c) E. J. Corey, M. F. Semmelhack, J. Am. Chem. Soc.
1967, 89, 2755.S; d) b) E. J. Corey, L. S. Hegedus, M. F. Semmelhack,
J. Am. Chem. Soc. 1968, 90, 2417.
For selected examples of formation of all carbon quaternary centers via
neuclophile/electrophle C(sp3)-C(sp2) coupling, see: a) A. Joshi-Pangu,
C.‒Y. Wang, M. R. Biscoe, J. Am. Chem. Soc. 2011, 133, 8478; Cu-
catalyzed coupling of tertiary R-ZnX with hetero-aryl iodides, see: b) S.
Thapa, A. Kafle, S. K. Gurung, A. Montoya, P. Riedel, R. Giri, Angew.
Chem. Int. Ed. 2015, 54, 8236; Coupling of tert-alkyl halides with Ar-9-
BBN: c) S. L. Zultanski, G. C. Fu, J. Am. Chem. Soc. 2013, 135, 624.
This article is protected by copyright. All rights reserved.