Organic Letters
Letter
(5) (a) Sasakura, K.; Sugasawa, T. Heterocycles 1981, 15, 421−425.
(b) Majer, P.; Slaninova, J.; Lebl, M. Int. J. Peptide Protein Res. 1994, 43,
62−68. (c) Jiu, J.; Mizuba, S.; Hribar, J. Appl. Environ. Microbiol. 1977,
33, 26−30.
(6) (a) Yamazaki, S. Chem. Lett. 1992, 823−826. (b) Hu, Z.; Kerton, F.
M. Org. Biomol. Chem. 2012, 10, 1618−1624. (c) Zhang, E.; Tian, H.;
Xu, S.; Yu, X.; Xu, Q. Org. Lett. 2013, 15, 2704−2707.
(7) Wu, X. F.; Bheeter, C. B.; Neumann, H.; Dixneuf, P. H.; Beller, M.
Chem. Commun. 2012, 48, 12237−12239.
(8) (a) Goti, A.; Cardona, F.; Soldaini, G. Org. Synth. 2005, 81, 204.
(b) Gella, C.; Ferrer, E.; Alibes, R.; Busque, F.; March, P. D.; Figueredo,
M.; Font, J. J. Org. Chem. 2009, 74, 6365−6367.
this novel protocol and study of a detailed mechanism are currently
underway.
ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedures, full characterization of new products,
and copies of NMR spectra. This material is available free of
AUTHOR INFORMATION
Corresponding Author
■
(9) Dols, P. P. M. A.; Folmer, B. J. B.; Hermkens,P.H. H.; Lucas, H.; Ma
Rewinkel, J. B. WO 2003084963, 16 October 2003.
(10) Laha, J. K.; Tummalapalli, K. S. S.; Gupta, A. Eur. J. Org. Chem.
2013, 36, 8330−8335.
Notes
(11) (a) Yang, Z.; Chen, X.; Wang, S.; Liu, J.; Xie, K.; Wang, A.; Tan, Z.
J. Org. Chem. 2012, 77, 7086−7091. (b) Yang, Z.; Wang, A.; Chen, X.;
Gui, Q.; Liu, J.; Tan, Z.; Wang, H.; Shi, J.-W. Synlett. 2013, 24, 1549−
1554.
(12) (a) Yan, J.; Travis, B. R.; Borhan, B. J. Org. Chem. 2004, 69, 9299−
9302. (b) Moriyama, K.; Takemura, M.; Togo, H. Org. Lett. 2012, 14,
2414−2417.
(13) Qiu, J.; Zhang, R. Org. Biomol. Chem. 2013, 11, 6008−6012.
(14) Chianese, A. R.; Zeglis, B. M.; Crabtree, R. H. Chem. Commun.
2004, 2176−2177.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We greatly appreciate financial support from the CSIR, New
Delhi. K.S.S.T. and A.G. thank the CSIR, New Delhi, for the
award of Senior Research and Research Associate fellowships,
respectively. J.K.L. thanks Prof. Satinder V. Kessar, Panjab
University, for insightful discussions.
(15) (a) Huyser, E. S.; Rose, L. G. J. Org. Chem. 1972, 37, 851−853.
(b) Ogawa, K.; Nomura, Y.; Takeuchi, Y.; Tomoda, S. J. Chem. Soc.,
Perkin Trans. 1 1982, 3031−3035.
(16) (a) Black, D.; Rothnie, N. E. Aust. J. Chem. 1983, 36, 1149−1157.
For imine formation with a related dibenzodiazepine, see: (b) Ishizumi,
K.; Mori, K.; Inaba, S.; Yamamoto, H. Chem. Pharm. Bull. 1975, 23,
2169−2173.
(17) Addition of H2SO4 to the imine 31 was suggested by one of the
reviewers.
REFERENCES
■
(1) For review, see: (a) Wang, T.; Jiao, N. Acc. Chem. Res. 2014, 47,
1137−1145. For some recent reports on C−C bond cleavage, see:
(b) Qin, C.; Zhou, W.; Chen, F.; Ou, Y.; Jiao, N. Angew. Chem., Int. Ed.
2011, 50, 12595−12599. (c) Cai, S.; Zhao, X.; Wang, X.; Liu, Q.; Li, Z.;
Wang, D. Z. Angew. Chem., Int. Ed. 2012, 51, 8050−8053. (d) Liu, H.;
Dong, C.; Zhang, Z.; Wu, P.; Jiang, X. Angew. Chem., Int. Ed. 2012, 51,
12570−12574. (e) Wang, Z.; Zhu, L.; Yin, F.; Su, Z.; Li, Z.; Li, C. J. Am.
Chem. Soc. 2012, 134, 4258−4263. (f) Yin, F.; Wang, Z.; Li, Z.; Li, C. J.
Am. Chem. Soc. 2012, 134, 10401−10404. (g) Liu, X.; Wang, Z.; Cheng,
X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330−14333. (h) Li, W.; Zheng,
X.; Li, Z. Adv. Synth. Catal. 2013, 355, 181−190. (i) Sun, H.; Yang, C.;
Gao, F.; Li, Z.; Xia, W. Org. Lett. 2013, 15, 624−627. (j) More, N. Y.;
Jeganmohan, M. Org. Lett. 2014, 16, 804−807. (k) Tang, C.; Jiao, N.
Angew. Chem., Int. Ed. 2014, 53, 6528−6532. (l) Lewis, C. A.;
Wolfenden, R. J. Am. Chem. Soc. 2014, 136, 130−136. (m) Sun, J.;
Tan, Q.; Yang, W.; Liu, B.; Xu, B. Adv. Synth. Catal. 2014, 356, 388−394.
(n) Maji, A.; Rana, S.; Akanksha; Maiti, D. Angew. Chem., Int. Ed. 2014,
53, 2428−2432.
(18) For K2S2O8-mediated decarboxylation, see: Brown, P. M.; Dewar,
P. S.; Forrester, A. R.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1
1972, 2842−2846. (b) Tanner, D. D.; Osman, S. A. A. J. Org. Chem.
1987, 52, 4689−4693. (c) Seo, S.; Slater, M.; Greaney, M. F. Org. Lett.
2012, 14, 2650−2653.
(19) See the Supporting Information for the preparation of compound
35.
(2) For some recent reports on C−N bond cleavage, see: (a) Ueno, S.;
Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098−6099.
(b) Liu, C.-R.; Li, M.-B.; Cheng, D.-J.; Yang, C.-F.; Tian, S.-K. Org. Lett.
2009, 11, 2543−2545. (c) Sabiah, S.; Lee, C.-S.; Hwang, W-.S.; Lin, I. J.
B. Organometallics 2010, 29, 290−293. (d) Zhu, M.-K.; Zhao, J.-F.; Loh,
T.-P. Org. Lett. 2011, 13, 6308−6311. (e) Liu, C.-R.; Wang, T.-T.; Qi,
Q-.B.; Tian, S.-K. Chem. Commun. 2012, 48, 10913−10915. (f) Wang,
Y.; Chi, Y.; Zhang, W.-X.; Xi, Z. J. Am. Chem. Soc. 2012, 134, 2926−2929.
(g) Liang, D.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2013, 15, 3476−3479.
(h) Huang, H.; Ji, X.; Wu, W.; Huang, L.; Jiang, H. J. Org. Chem. 2013,
78, 3774−3782. (i) Zhang, J.; Jiang, J.; Li, Y.; Wan, X. J. Org. Chem. 2013,
78, 11366−11372. (j) Zhang, X.; Yang, W.; Wang, L. Org. Biomol. Chem.
2013, 11, 3649−3654. (k) Abe, M.; Watanabe, S.; Tamura, H.;
Boinapally, S.; Kanahara, K.; Fujiwara, Y. J. Org. Chem. 2013, 78, 1940−
1948. (l) Sharma, S.; Han, S.; Kim, M.; Mishra, N. K.; Park, J.; Shin, Y.;
Ha, J.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Org. Biomol. Chem. 2014, 12,
1703−1706. (m) Tobisu, M.; Nakamura, K.; Chatani, N. J. Am. Chem.
Soc. 2014, 136, 5587−5590.
(3) For some recent reports on both C−C and C−N bond cleavage,
see: (a) Feng, P.; Sun, X.; Su, Y.; Li, X.; Zhang, L.-H.; Shi, X.; Jiao, N.
Org. Lett. 2014, 16, 3388−3391. (b) Li, C.; Zhang, W.-T.; Wang, X.-S. J.
Org. Chem. 2014, 79, 5847−5851.
(4) Laha, J. K.; Tummalapalli, K. S. S.; Gupta, A. Eur. J. Org. Chem.
2014, 37, 4773−4779.
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