10.1002/chem.201801537
Chemistry - A European Journal
FULL PAPER
Keywords: Annulation reaction
•
spiro-naphthalenones
•
dearomatization • C-H activation • ruthenium catalysis
[1]
[2]
For selected reviews on spiro compounds, see: (a) G. S. Singh, Z. Y.
Desta, Chem. Rev. 2012, 112, 6104; (b) V. A. D’yakonov, O. A.
Trapeznikova, A. de Meijere, U. M. Dzhemilev, Chem. Rev. 2014, 114,
5775; (c) E. M. Carreira, T. C. Fessard, Chem. Rev. 2014, 114, 8257.
(a) N. W. Gaikwad, G.-S. Hwang, I. H. Goldberg, Org. Lett. 2004, 6,
4833; (b) Y. Lin, G. B. Jones, Org. Lett. 2005, 7, 71; (c) J. R. Allen, K.
Biswas, M. C. Bryan, R. Burli, G.-Q. Cao, M. J. Frohn, J. E. Golden, S.
Mercede, S. Neira, T. Peterkin, A. J. Pickrell, A. Reed, C. M. Tegley, X.
Wang, PCT Int. Appl., 2008076427, 26 Jun 2008; (d) T. R. R. Pettus, M.
Inoue, X.-T. Chen, S. J. Danishefsky, J. Am. Chem. Soc., 2000, 122,
6160; (e) D. M. James, H. B. Kunze, D. J. Faulkner, J. Nat. Prod. 1991,
54, 1137; (f) P. S. Manchand, J. F. Blount, J. Chem. Soc. Chem.
Commun. 1975, 894.
[3]
For selected recent reviews and examples on C-H activation, see: (a)
D.-S. Kim, W.-J. Park, C.-H. Jun, Chem. Rev. 2017, 117, 8977; (b) M.
Moselage, J. Li, L. Ackermann, ACS Catal. 2016, 6, 498; (c) J. He, M.
Wasa, K. S. L. Chan, Q. Shao, J.-Q. Yu, Chem. Rev. 2017, 117, 8754;
(d) P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112,
5879; (e) B. Li, P. H. Dixneuf, Chem. Soc. Rev. 2013, 42, 5744; (f) W.
Inoue, Org. Lett. 2005, 7, 4009; (h) L. Ackermann, R. Born, P. Álvarez-
Bercedo, Angew. Chem., Int. Ed. 2007, 46, 6364; (i) L. Ackermann, R.
Vicente, H. K. Potukuchi, V. Pirovano, Org. Lett. 2010, 12, 5032; (j) D.
Zell, S. Warratz, D. Gelman, S. J. Garden, L. Ackermann, Chem. Eur. J.
2016, 22,1248; (k) B. Štefane, H. B. Žugelj, U. Grošelj, P. Kuzman, J.
Svete, F. Požgan, Eur. J. Org. Chem. 2017, 1855; (l) V. P. Boyarskiy, D.
S. Ryabukhin, N. A. Bokach, A. V. Vasilyev, Chem. Rev. 2016, 116,
5894; (m) J. Wu, W. Xu, Z.-X. Yu, J. Wang, J. Am. Chem. Soc. 2015,
137, 9489; (n) J.-L. Yu, S.-Q. Zhang, X. Hong, J. Am. Chem. Soc. 2017,
139, 7224; (o) A. Bechtoldt, C. Tirler, K. Raghuvanshi, S. Warratz, C.
Kornhaaß, L. Ackermann, Angew. Chem. Int. Ed. 2016, 55, 264.
(a) M. R. Kuram, M. Bhanuchandra, A. K. Sahoo, Angew. Chem., Int. Ed.
2013, 52, 4607; (b) R. Zhu, J. B. Wei, Z. J. Shi, Chem. Sci. 2013, 4,
3706; (c) B. M. Trost, F. D. Toste, K. Greenman, J. Am. Chem. Soc.
2003, 125, 4518; (d) J. Nan, Z. Zuo, L. Luo, L. Bai, H. Zheng, Y. Yuan,
J. Liu, X. Luan, Y. Wang, J. Am. Chem. Soc. 2013, 135, 17306; (e) V. S.
Thirunavukkarasu, M. Donati, L. Ackermann, Org. Lett. 2012, 14, 3416;
J. Am. Chem. Soc. 2015, 137, 4880; (h) S. Kujawa, D. Best, D. J. Burns,
H. W. Lam, Chem. Eur. J. 2014, 20, 8599; (i) H. Zheng, L. Bai, J. Liu, J.
Nan, Z. Zuo, L. Yang, Y. Wang, X. Luan, Chem. Commun. 2015, 51,
3061.
[4]
[5]
[6]
A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J.
Am. Chem. Soc. 2014, 136, 834.
(a) P. P. Kaishap, B. Sarma, S. Gogoi, Chem. Commun. 2016, 52, 9809;
(b) S. Baruah, S. Borthakur, S. Gogoi, Chem. Commun. 2017, 53,
9133; (c) P. P. Kaishap, G. Duarah, B. Sarma, D. Chetia, S. Gogoi,
Angew. Chem., Int. Ed., 2017, DOI: 10.1002/ange.201710049.
A. Rudolph, P. H. Bos, A. Meetsma, A. J. Minnaard, B. L Feringa,.
Angew. Chem., Int. Ed. 2011, 50, 5834.
[7]
[8]
[9]
S. Gu, L. Luo, J. Liu, L. Bai, H. Zheng, Y. Wang, X. Luan, Org. Lett.
2014, 16, 6132.
F. Romanov-Michailidis, L. Guénée, A. Alexakis, Org. Lett., 2013, 15,
5890.
[10] CCDC 1578367 contains the crystallographic data of 3ad and CCDC
1578368 contains the crystallographic data of 3ea.
[11] E. M. Simmons, J. F. Hartwig, Angew. Chem., Int. Ed. 2012, 51, 3066.
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