Organic Letters
Letter
Adv. Synth. Catal. 2015, 357, 901. (h) Yoshida, T.; Mori, K. Chem.
Commun. 2017, 53, 4319. (i) Machida, M.; Mori, K. Chem. Lett. 2018,
47, 868. (j) Yokoo, K.; Mori, K. Chem. Commun. 2018, 54, 6927.
(k) Hisano, N.; Kamei, Y.; Kansaku, Y.; Yamanaka, M.; Mori, K. Org.
Lett. 2018, 20, 4223. (l) Yoshida, T.; Mori, K. Chem. Commun. 2018,
54, 12686. (m) Tamura, R.; Kitamura, E.; Tsutsumi, R.; Yamanaka,
M.; Akiyama, T.; Mori, K. Org. Lett. 2019, 21, 2383 For an
asymmetric version of the internal redox reaction catalyzed by chiral
phosphoric acid, see: . (n) Mori, K.; Ehara, K.; Kurihara, K.; Akiyama,
T. J. Am. Chem. Soc. 2011, 133, 6166.
(8) For selected examples of the internal redox reactions, see:
(a) Pastine, S. J.; McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2005,
127, 12180. (b) Pastine, S. J.; Sames, D. Org. Lett. 2005, 7, 5429.
(c) Zhang, C.; De, C. K.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008,
130, 416. (d) Zhang, C.; Murarka, S.; Seidel, D. J. Org. Chem. 2009,
74, 419. (e) McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2009, 131,
402. (f) Ruble, J. C.; Hurd, A. R.; Johnson, T. A.; Sherry, D. A.;
Barbachyn, M.; Toogood, R. P. L.; Bundy, G. L.; Graber, D. R.;
Kamilar, G. M. J. Am. Chem. Soc. 2009, 131, 3991. (g) Mahoney, M.
J.; Moon, D. T.; Hollinger, J.; Fillion, E. Tetrahedron Lett. 2009, 50,
4706. (h) McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11,
2972. (i) Yang, S.; Li, Z.; Jian, X.; He, C. Angew. Chem., Int. Ed. 2009,
48, 3999. (j) Vadola, P. A.; Sames, D. J. Am. Chem. Soc. 2009, 131,
16525. (k) Alajarin, M.; Marin-Luna, M.; Vidal, A. Adv. Synth. Catal.
Yabe, S.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2014, 136,
3744. (c) Mori, K.; Umehara, N.; Akiyama, T. Chem. Sci. 2018, 9,
7327.
(12) For the formation of a seven-membered ring by the [1,5]-
hydride shift, see: (a) Zhou, G.; Zhang, J. Chem. Commun. 2010, 46,
6593. (b) Haibach, M. C.; Deb, I.; De, C. K.; Seidel, D. J. Am. Chem.
Soc. 2011, 133, 2100. (c) Chang, Y.-Z.; Li, M.-L.; Zhao, W.-F.; Wen,
X.; Sun, H.; Xu, Q.-L. J. Org. Chem. 2015, 80, 9620. (d) Suh, C. W.;
Kwon, S. J.; Kim, D. Y. Org. Lett. 2017, 19, 1334. (e) Li, S.-S.; Zhou,
L.; Wang, L.; Zhao, H.; Yu, L.; Xiao, J. Org. Lett. 2018, 20, 138.
(13) For examples of the internal redox reactions involving the
[1,6]-hydride shift, see: (a) Reinhoudt, D. N.; Visser, G. W.;
Verboom, W.; Benders, P. H.; Pennings, M. L. M. J. Am. Chem. Soc.
1983, 105, 4775. (b) De Boeck, B.; Jiang, S.; Janousek, Z.; Viehe, H.
G. Tetrahedron 1994, 50, 7075. (c) De Boeck, B.; Janousek, Z.; Viehe,
H. G. Tetrahedron 1995, 51, 13239. (d) Che, X.; Zheng, L.; Dang, Q.;
̈
́
́
Bai, X. Synlett 2008, 2008, 2373. (e) Foldi, A. A.; Ludanyi, K.; Benyei,
́
A. C.; Matyus, P. Synlett 2010, 2010, 2109 See also refs 7c and 11b. .
(14) For examples of the internal redox reactions involving the
́
́
[1,7]-hydride shift, see: Polonka-Balint, A.; Saraceno, C.; Ludanyi, K.;
́
́
Benyei, A.; Matyus, P. Synlett 2008, 2008, 2846.
(15) In our previous study (ref 11a), we found that Brønsted acids
were ineffective because of the formation of ammonium salt between
the Brønsted acids and the tertiary amine in the substrate.
(16) (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem.,
Int. Ed. 2004, 43, 1566. (b) Uraguchi, D.; Terada, M. J. Am. Chem.
Soc. 2004, 126, 5356.
̈
2011, 353, 557. (l) Jurberg, I. D.; Peng, B.; Wostefeld, E.; Wasserloos,
M.; Maulide, N. Angew. Chem., Int. Ed. 2012, 51, 1950. (m) Han, Y.-
Y.; Han, W.-Y.; Hou, X.; Zhang, X.-W.; Yuan, W.-C. Org. Lett. 2012,
14, 4054. (n) Gao, X.; Gaddam, V.; Altenhofer, E.; Tata, R. R.; Cai,
Z.; Yongpruksa, N. A.; Garimallaprabhakaran, K.; Harmata, M. Angew.
Chem., Int. Ed. 2012, 51, 7016. (o) Chen, D.-F.; Han, Z.-Y.; He, Y.-P.;
Yu, J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 12307.
(p) Dieckmann, A.; Richers, M. T.; Platonova, A. Y.; Zhang, C.;
Seidel, D.; Houk, N. K. J. Org. Chem. 2013, 78, 4132. (q) Alajarin, M.;
Bonillo, B.; Marin-Luna, M.; Sanchez-Andrada, P.; Vidal, A. Chem. -
Eur. J. 2013, 19, 16093. (r) Vidal, A.; Marin-Luna, M.; Alajarin, M.
Eur. J. Org. Chem. 2014, 2014, 878. (s) Zhu, S.; Chen, C.; Xiao, M.;
Yu, L.; Wang, L.; Xiao, J. Green Chem. 2017, 19, 5653. (t) Lu, X.-L.;
Lyu, M.-Y.; Peng, X.-S.; Wong, H. N. C. Angew. Chem., Int. Ed. 2018,
57, 11365. (u) Wang, S.; An, X. D.; Li, S. S.; Liu, X.; Liu, Q.; Xiao, J.
Chem. Commun. 2018, 54, 13833. (v) Li, S.-S.; Zhu, S.; Chen, C.;
Duan, K.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21, 1058. (w) Zhao, S.;
Wang, X.; Wang, P.; Wang, G.; Zhao, W.; Tang, X.; Guo, M. Org. Lett.
2019, 21, 3990. (x) Paul, A.; Seidel, D. J. Am. Chem. Soc. 2019, 141,
8778.
(17) For details of the examination of the reaction conditions for
asymmetric reaction, see the SI.
(9) For examples of the enantioselective internal redox reactions,
see: (a) Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. J. Am. Chem. Soc.
2009, 131, 13226. (b) Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am.
Chem. Soc. 2010, 132, 11847. (c) Cao, W.; Liu, X.; Wang, W.; Lin, L.;
Feng, X. Org. Lett. 2011, 13, 600. (d) Zhou, G.; Liu, F.; Zhang, J.
Chem. - Eur. J. 2011, 17, 3101. (e) He, Y.-P.; Du, Y.-L.; Luo, S.-W.;
Gong, L. Z. Tetrahedron Lett. 2011, 52, 7064. (f) Chen, L.; Zhang, L.;
Lv, Z.; Cheng, J.-P.; Luo, S. Chem. - Eur. J. 2012, 18, 8891. (g) Jiao,
Z.-W.; Zhang, S.-Y.; He, C.; Tu, Y.-Q.; Wang, S.-H.; Zhang, F.-M.;
Zhang, Y.-Q.; Li, H. Angew. Chem., Int. Ed. 2012, 51, 8811. (h) Kang,
Y. K.; Kim, D. Y. Adv. Synth. Catal. 2013, 355, 3131. (i) Kang, Y. K.;
Kim, D. Y. Chem. Commun. 2014, 50, 222. (j) Suh, C. W.; Kim, D. Y.
Org. Lett. 2014, 16, 5374. (k) Cao, W.; Liu, X.; Guo, J.; Lin, L.; Feng,
X. Chem. - Eur. J. 2015, 21, 1632 See also refs 7n and 11a. .
(10) These types of reactions are classified as the “tert-amino effect.”
For reviews, see: (a) Meth-Cohn, O.; Suschitzky, H. Adv. Heterocycl.
Chem. 1972, 14, 211. (b) Verboom, W.; Reinhoudt, D. N. Recl. Trav.
Chim. Pays-Bas 1990, 109, 311. (c) Meth-Cohn, O. Adv. Heterocycl.
Chem. 1996, 65, 1. (d) Quintela, J. M. Recent Res. Dev. Org. Chem.
́
́
́
́
2003, 7, 259. (e) Matyus, P.; Elias, O.; Tapolcsanyi, P.; Polonka-
́
́
́
Balint, A.; Halasz-Dajka, B. Synthesis 2006, 2006, 2625.
(11) For the double C(sp3)−H bond functionalization by sequential
utilization of the internal redox reaction developed by our group, see:
(a) Mori, K.; Isogai, R.; Kamei, Y.; Yamanaka, M.; Akiyama, T. J. Am.
Chem. Soc. 2018, 140, 6203 See also: . (b) Mori, K.; Kurihara, K.;
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Org. Lett. XXXX, XXX, XXX−XXX