Communication
ChemComm
(i) H.-P. Bi, L. Zhao, Y.-M. Liang and C.-J. Li, Angew. Chem., Int. Ed.,
2009, 48, 792; ( j) H.-P. Bi, W.-W. Chen, Y.-M. Liang and C.-J. Li, Org.
Lett., 2009, 11, 3246; (k) H.-P. Bi, Q. Teng, M. Guan, W.-W. Chen,
Y.-M. Liang, X. Yao and C.-J. Li, J. Org. Chem., 2010, 75, 783.
5 (a) Y. Yan and Z. Wang, Chem. Commun., 2011, 47, 9513;
(b) Q. Wang, C. Wan, Y. Gu, J. Zhang, L. Gao and Z. Wang, Green
Chem., 2011, 13, 578; (c) Q. Wang, S. Zhang, F. Guo, B. Zhang, P. Hu
and Z. Wang, J. Org. Chem., 2012, 77, 11161.
6 For selected examples, see: (a) Z. Zuo and D. W. C. MacMillan, J. Am.
Chem. Soc., 2014, 136, 5257; (b) L. Chu, C. Ohta, Z. Zuo and
D. W. C. MacMillan, J. Am. Chem. Soc., 2014, 136, 10886;
(c) A. Noble and D. W. C. MacMillan, J. Am. Chem. Soc., 2014,
136, 11602; (d) F. Gao, J.-T. Wang, L.-L. Liu, N. Ma, C. Yang,
Y. Gao and W. Xia, Chem. Commun., 2017, 53, 8533; (e) J. Li,
Q. Lefebvre, H. Yang, Y. Zhao and H. Fu, Chem. Commun., 2017,
53, 10299; ( f ) S. J. McCarver, J. X. Qiao, J. Carpenter, R. M. Borzilleri,
M. A. Poss, M. D. Eastgate, M. Miller and D. W. C. MacMillan, Angew.
Chem., Int. Ed., 2017, 56, 728; (g) Y. Yoshimi, M. Masuda,
T. Mizunashi, K. Nishikawa, K. Maeda, N. Koshida, T. Itou,
T. Morita and M. Hatanaka, Org. Lett., 2009, 11, 4652;
(h) K. Nishikawa, T. Ando, K. Maeda, T. Morita and Y. Yoshimi,
Org. Lett., 2013, 15, 636.
7 (a) Z. Zuo, D. T. Ahneman, L. Chu, J. A. Terrett, A. G. Doyle and
D. W. C. MacMillan, Science, 2014, 345, 437; (b) A. Noble,
S. J. McCarver and D. W. C. MacMillan, J. Am. Chem. Soc., 2015,
137, 624; (c) Z. Zuo, H. Cong, W. Li, J. Choi, G. C. Fu and
D. W. C. MacMillan, J. Am. Chem. Soc., 2016, 138, 1832;
(d) A. Millet, Q. Lefebvre and M. Rueping, Chem. – Eur. J., 2016,
22, 13464.
Scheme 3 Visible light-induced oxidative decarboxylative Chichibabin
pyridinium synthesis of ficuseptine.
(one C–N and two C–C bonds) by a cascade visible light-induced
decarboxylative Chichibabin pyridine synthesis and provides
a straightforward method to prepare highly functionalized
pyridiniums.
This work was financially supported by the Natural Science
Foundation of Yunnan Province (2018FY001015 and 2019FB133),
the National Natural Science Foundation of China (21871228),
and the Program for Changjiang Scholars and Innovative
Research Team in University (IRT_17R94). We are grateful to
Prof. Zhi-Xiang Yu and Dr Guang-Yu Zhang of Peking University
for the help with the Gibbs energy profile calculations.
8 (a) M. Silvi, E. Arceo, I. D. Jurberg, C. Cassani and P. Melchiorre,
J. Am. Chem. Soc., 2015, 137, 6120; (b) A. Bahamonde and
P. Melchiorre, J. Am. Chem. Soc., 2016, 138, 8019; (c) G. Filippini,
M. Silvi and P. Melchiorre, Angew. Chem., Int. Ed., 2017, 56, 4447.
9 (a) I. M. Dixon, J.-P. Collin, J.-P. Sauvage, L. Flamigni, S. Encinas and
F. Barigelletti, Chem. Soc. Rev., 2000, 29, 385; (b) N. A. Romero and
D. A. Nicewicz, Chem. Rev., 2016, 116, 10075.
10 (a) L. Yu, D. Chen, J. Li, J. Ramirez, P. G. Wang and S. G. Bott, J. Org.
Chem., 1997, 62, 208; (b) N. Z. Burns and P. S. Baran, Angew. Chem.,
Int. Ed., 2008, 47, 205; (c) N. Z. Burns, M. Jessing and P. S. Baran,
Tetrahedron, 2009, 65, 6600; (d) F. Dagorn, L.-H. Yan, E. Gravel,
K. Leblanc, A. Maciuk and E. Poupon, Tetrahedron Lett., 2011,
52, 3523; (e) T. Usuki, T. Sugimura, A. Komatsu and Y. Koseki,
Org. Lett., 2014, 16, 1672; ( f ) T. Pesnot, M. C. Gershater,
M. Edwards, J. M. Ward and H. C. Hailes, Molecules, 2017,
22, 626; (g) C. Allais, J.-M. Grassot, J. Rodriguez and
T. Constantieux, Chem. Rev., 2014, 114, 10829; (h) B. B. Snider and
B. J. Neubert, Org. Lett., 2005, 7, 2715; (i) N. Tanaka, M. Kurita,
Y. Murakami and T. Usuki, Eur. J. Org. Chem., 2018, 6002;
( j) A. Imura, N. Tanaka and T. Usuki, Tetrahedron Lett., 2019,
60, 489.
Conflicts of interest
There are no conflicts to declare.
Notes and references
1 (a) J. Schwarz and B. Koenig, Green Chem., 2018, 20, 323;
(b) G. J. P. Perry and I. Larrosa, Eur. J. Org. Chem., 2017, 3517;
(c) Y. Wei, P. Hu, M. Zhang and W. Su, Chem. Rev., 2017, 117, 8864;
(d) F. Sandfort, M. J. O’Neill, J. Cornella, L. Wimmer and P. S. Baran,
Angew. Chem., Int. Ed., 2017, 56, 3319; (e) M. O. Konev and
E. R. Jarvo, Angew. Chem., Int. Ed., 2016, 55, 11340; ( f ) J. Xuan,
Z.-G. Zhang and W.-J. Xiao, Angew. Chem., Int. Ed., 2015, 54, 15632.
2 S. Mandal, T. Bera, G. Dubey, J. Saha and J. K. Laha, ACS Catal.,
2018, 8, 5085.
3 (a) I. Coldham and R. Hufton, Chem. Rev., 2005, 105, 2765;
(b) G. Pandey, P. Banerjee and S. R. Gadre, Chem. Rev., 2006,
106, 4484.
4 (a) C. Zhang and D. Seidel, J. Am. Chem. Soc., 2010, 132, 1798;
(b) D. Seidel, Acc. Chem. Res., 2015, 48, 317; (c) D. Das, M. T. Richers,
L. Ma and D. Seidel, Org. Lett., 2011, 13, 6584; (d) Y. Kang and
D. Seidel, Org. Lett., 2016, 18, 4277; (e) A. Paul, N. R. Thimmegowda,
T. G. Cruz and D. Seidel, Org. Lett., 2018, 20, 602; ( f ) K. B. Manjappa,
W.-F. Jhang, S.-Y. Huang and D.-Y. Yang, Org. Lett., 2014, 16, 5690;
(g) S. U. Dighe, K. S. Anil Kumar, S. Srivastava, P. Shukla, S. Singh,
M. Dikshit and S. Batra, J. Org. Chem., 2015, 80, 99; (h) D. Yang,
D. Zhao, L. Mao, L. Wang and R. Wang, J. Org. Chem., 2011, 76, 6426;
11 (a) H.-Y. Jang, J.-B. Hong and D. W. C. MacMillan, J. Am. Chem. Soc.,
2007, 129, 7004; (b) H. Kim and D. W. C. MacMillan, J. Am. Chem.
Soc., 2008, 130, 398; (c) T. H. Graham, C. M. Jones, N. T. Jui and
D. W. C. MacMillan, J. Am. Chem. Soc., 2008, 130, 16494.
12 B. Baumgartner, C. A. J. Erdelmeier, A. D. Wright, T. Rali and
O. Sticher, Phytochemistry, 1990, 29, 3327.
13 R. Ott-Longoni, N. Viswanathan and M. Hesse, Helv. Chim. Acta,
1980, 63, 2119.
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