4
Tetrahedron Letters
10. a) Girard, N.; Hurvois, J.-P.; Toupet, L.; Moinet, C. Synth.
this is the first example of the use of Na2S2O8 to promote CDC
Commun. 2005, 35, 711; b) Girard, N.; Gautier, C.; Malassene, R.;
Hurvois, J.-P.; Moinet, C.; Toupet, L. Synlett 2004, 2005; c)
Girard, N.; Hurvois, J.-P. Tetrahedron Lett. 2007, 48, 4097.
11. a) Eustache, J.; Van de Weghe, P.; Nouen, D. L.; Uyehara, H.;
Kabuto, C.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4043; b)
Tarver, J. E., Jr.; Pfizenmayer, A. J.; Joullié, M. M. J. Org. Chem.
2001, 66, 7575; c) Vecchietti, V.; Clarke, G. D.; Colle, R.;
Giardina, G.; Petrone, G.; Sbacchi, M. J. Med. Chem. 1991, 34,
2624.
12. a) Richter, H.; García Mancheño, O. Eur. J. Org. Chem. 2010,
4460; b) Richter, H.; Fröhlich, R.; Daniliuc, C.-G.; García
Mancheño, O. Angew. Chem. Int. Ed. 2012, 51, 8656; c) Ghobrial,
M.; Harhammer, K.; Mihovilovic, M. D.; Schnürch, M. Chem.
Commun. 2010, 46, 8836; d) Ghobrial, M.; Schnürch, M.;
Mihovilovic, M. D. J. Org. Chem. 2011, 76, 8781; e) Schweitzr-
Chaput, B.; Klussmann, M. Eur. J. Org. Chem. 2013, 666; f)
Schweitzr-Chaput, B.; Sud, A.; Pintér, Á; Dehn, S.; Schulze, P.;
Klussmann, M. Angew. Chem. Int. Ed. 2013, 52, 13228; g) Li, X.
G.; Sun, B.; Xie, Z. Y.; Qin, X. J.; Liu, L.; Lou, H. X. J. Org.
Chem. 2013, 78, 3104.
13. a) Walling, C.; Zhao, C.; El-Taliawi, G. M. J. Org. Chem. 1983,
48, 4910; b) Parliament, T. H.; Parliament, M. W.; Fagerson, I. S.,
Chem. Ind. (London) 1966, 1845; c) Dhar, D. N.; Munjal, R. C.
Synthesis 1973, 542; d) Moritz, C.; Wolffenstein, R. Chem. Ber.
1899, 32, 432; e) Bacon, R. G. R.; Doggart, J. R.; J. Chem. Soc.
1960, 1332; f) Austin, P. C. J. Chem. Soc. 1911, 99, 262.
14. To facilitate the purifications, the obtained aldehydes were
reduced by NaBH4 in MeOH to afford alcohols 6f and 6h.
15. We thank the referee’s suggestion on the demonstration of the
gram-scale reaction.
−C bond formation.
reaction with carbamates, leading to C
The
development of other peroxydisulfate-mediated oxidative
coupling reactions is currently under investigation and will be
disclosed in due course.
Acknowledgments
Financial Support from the National Science Foundation of
China (No. 21202093), Young Scientist Foundation Grant of
Shandong Province (No. BS2013YY001) and Changjiang
Scholars and Innovative Research Team (IRT13028) is greatly
appreciated.
Supplementary Material
The spectra of the products associated with this manuscript
can be found in the supporting information.
References and notes
1. a) Shamma, M.; Moniot, J. L. The Isoquinoline Alkaloids,
Chemistry and Pharmacology, Academic Press, New York and
London, 1972; b) Welsch, M. E.; Snyder, S. A.; Stockwell, B. R.
Curr. Opin. Chem. Biol., 2010, 14, 437; c) Herbert, R. B. in The
Chemistry and Biology of Isoquinoline Alkaloids, (Eds:
Phillipson, J. D.; Roberts, M. F.; Zenk, M. H.), Springer Verlag,
Berlin, Heidelberg, New York, Tokyo, 1985, 213.
2. a) Ohtaka, A.; Ukai, M.; Hatanaka, T.; Kobayashi, S.; Ikeda, K.;
Sato, S.; Miyata, K.; Sasamata, M. Eur. J. Pharmacol. 2004, 492,
243; b) Cardozo, L. Lisec, M.; Millard, R.; Trip, O. V.; Kuzmin, I.;
Drogendijk, T. E.; Huang, M.; Ridder, A. M. J. Urology 2004, 172,
1919; c) Smulders, R. A.; Krauwinkel, W. J.; Swart, P. J.; Huang,
M. J. Clin. Pharmacol. 2004, 44, 1023.
3. Wanner, K. T.; Praschak, I.; Höfner, G.; Beer, H. Arch. Pharm.
1996, 329, 11.
4. a) Rozwadowska, M. D. Heterocycles 1994, 39, 903; b) Czarnocki,
Z. A.; Siwicka, A.; Szawkalo, J. Curr. Org. Synth. 2005, 2, 301; c)
Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104,
3341; d) Bentley, K. W. Nat. Prod. Rep. 2005, 22, 249.
5. a) Fishlock, D.; Williams, R. M. J. Org. Chem. 2008, 73, 9594; b)
Youn, S. W. J. Org. Chem. 2006, 71, 2521; c) Silveria, C. C.;
Felix, L. A.; Braga, L. A.; Kaufman, T. S. Org. Lett. 2005, 7, 3701;
d) Gurjar, M. K.; Pramanik, C.; Bhattasali, D.; Ramana, C. V.;
Mohapatra, D. K. J. Org. Chem. 2007, 72, 6591; e) Wang, Y.-C.;
Georgjiou, P. E. Org. Lett. 2002, 4, 2675; f) Polniaszek, R. P.;
Kaufman, C. R. J. Am. Chem. Soc. 1989, 111, 4859; g) Zein, A. H.;
Dawe, L. N.; Georghiou, P. E. J. Nat. Prod. 2010, 73, 1427; h)
Zein, A. L.; Dakhil, O. O.; Dawe, L. N.; Georghiou, P. E.
Tetrahedron Lett. 2010, 51, 177.
6. a) Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc.
Chem. Res. 2008, 41, 40; b) Trost, B. M. Acc. Chem. Res. 2002,
35, 695.
7. For reviews on the C–H functionalization: a) Robertson, J.; Pillai,
J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94; b) Davies, H. M. L.
Angew. Chem. Int. Ed. 2006, 45, 6422; c) Gutekunst, W. R.;
Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976; d) Liu, L.;
Floreancig, P. E. Curr. Opin. Drug Discovery Dev. 2010, 13, 733.
8. For reviews on CDC reactions, see: a) Li, C. J. Acc. Chem. Res.
2009, 42, 335; b) Yoo, W. J.; Li, C. J. Top. Curr. Chem. 2010,
292, 281; c) Scheuermann, C. J. Chem. Asian J. 2010, 5, 436; d)
Klussmann, M.; Sureshkumar, D. Synthesis 2011, 353; e) Yeung,
C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
9. a) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810; b) Li, Z.;
Yu, R.; Li, H. Angew. Chem. Int. Ed. 2008, 47, 7497; c) Yang, F.;
Li, J.; Xie, J.; Huang, Z. Z. Org. Lett. 2010, 12, 5214; d) Hari, D.
P.; König, B. Org. Lett, 2011, 13, 3852; e) Boess, E.;
Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. J.
Am. Chem. Soc. 2011, 133, 8106; f) Boess, E.; Schmitz, C.;
Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317; g) Murahashi,
S. I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008,
130, 11005; h) Murahashi, S. I.; Komiya, N.; Terai, H.; Nakae, T.
J. Am. Chem. Soc. 2003, 125, 15312; i) Muramatsu, W.; Nakano,
K.; Li, C. J. Org. Lett. 2013, 15, 3650.