Chemistry - A European Journal
10.1002/chem.201802475
COMMUNICATION
Chem. Lett. 2007, 36, 172-173; c) W. C. P. Tsang, R. H. Munday, G.
Brasche, N. Zheng, S. L. Buchwald, J. Org. Chem. 2008, 73, 7603-7610;
d) J. A. Jordan-Hore, C. C. C. Johansson, M. Gulias, E. M. Beck, M. J.
Gaunt, J. Am. Chem. Soc. 2008, 130, 16184 e) S. H. Cho, J. Yoon, S.
Chang, J. Am. Chem. Soc. 2011, 133, 5996; f) S. W. Youn, J. H. Bihn, B.
S. Kim, Org. Lett. 2011, 13, 3738; g) S. Choi, T. Chatterjee, W. J. Choi,
Y. You, E. J. Cho, ACS Catal, 2015, 5, 4796-4802; h) A. K. Verma, A. K.
Danodia, R. K. Saunthwal, M. Patel, D. Choundhary, Org. Lett. 2015, 17,
Acknowledgements
This work was partially supported by the Sasagawa Scientific
Research Grant from The Japan Science Society.
Keywords: Dibenzothiophene • Palladium • C-H activation •
Disulfide • Cyclization
3658-3661.
[
[
9]
a) Y. Kuninobu, T. Yoshida, K. Takai, J. Org. Chem. 2011, 76, 7630-
[
1]
Selected examples: a) S. Martín-Santamaría, J.-J. Rodríguez, S.
Pascual-Teresa, S. Gordon, M. Bengtsson, I. Garrido-Laguna, B. Rubio-
Viqueira, P. P. López-Casas, M. Hidalgo, B. Pascual-Teresa, A. Ramos,
Org. Biomol. Chem. 2008, 6, 3486-3489; b) J. Gao, L. Li, Q. Meng, R. Li,
H. Jiang, H. Li, W. Hu, J. Mater. Chem. 2007, 17, 1421-1426; c) Y. Wang,
S. R. Parkin, J. Gierschner, M. D. Watson, Org. Lett. 2008, 10, 3307-
7376; b) Y. Kuninobu, K. Origuchi, K. Takai, Heterocycle, 2012, 12, 3029-
3034; c) K. Baba, M. Tobisu, N. Chatani, Angew. Chem. 2013, 125,
12108-12111; Angew. Chem. Int. Ed. 2013, 52, 11892-11895; d) Y. Cui,
L. Fu, J. Cao, Y. Deng, J. Jiang, Adv. Synth. Catal. 2014, 356, 1217-
1222; e) X. Wei, Z. Lu, X. Zhao, Z. Duan, F. Mathey, Angew. Chem. 2015,
127, 1603-1606; Angew. Chem. Int. Ed. 2015, 54, 1583-1586.
3310; d) S. H. Jeong, J. Y. Lee, J. Mater. Chem. 2011, 21, 14604-14609;
10] a) T. Ureshimo, T. Yoshida, Y. Kuninobu, K. Takai, J. Am. Chem. Soc.
010, 132, 14324-14326; b) Y. Kuninobu, K. Yamauchi, N. Tamura, T.
e) S. Zhang, Z. Qiao, Y. Chen, Y. Wang, R. M. Edkins, Z. Liu, H. Li, Q.
Fang, Org. Lett. 2014, 16, 342-345; f) S.-C. Dong, L. Zhang, J. Liang, L.-
S. Cui, Q. Li, Z.-Q. Jiang, L.-S. Liao, J. Phys. Chem. C 2014, 118, 2375-
2
Seiki, K. Takai, Angew. Chem. 2013, 125, 1560-1562; Angew. Chem. Int.
Ed. 2013, 52, 1520-1522; c) M. Murai, Y. Takeuchi, K. Yamaguchi, Y.
Kuninobu, K. Takai, Chem. Eur. J. 2016, 22, 6048-6058; d) M. Murai, R.
Okada, A. Nishiyama, K. Takai, Org. Lett. 2016, 18, 4380-4383; e) D.
Zhou, Y. Gao, B. Liu, Q. Tan, B. Xin, Org. Lett. 2017, 19, 4628-4631; f)
T. Shibata, N. Uno, T. Sasaki, H. Takano, T. Sato, K. S. Kanyiva, J. Org.
Chem. 2018, 83, 3426-3432;
2
384; g) A. Fukazawa, D. Kishi, Y. Tanaka, S. Seki, S. Yamaguchi,
Angew. Chem. 2013, 125, 12313-12317; Angew. Chem. Int. Ed. 2013,
2, 12091-12095
a) N. M. Cullinane, C. G. Davies, G. I. Davies, J. Chem. Soc. 1936, 1435-
437; b) H. Gilman, A. L. Jacoby, J. Org. Chem. 1938, 3, 108-119; c) K.-
5
[
2]
1
P. Zeller, H. Petersen, Synthesis 1975, 532-533; d) R. Sanz, Y.
Fernández, M. P. Castroviejo, A. Pérez, F. J. Fañanás, J. Org. Chem.
[
[
11] R. Samanta, A. P. Antonchick, Angew. Chem. 2011, 123, 5323-5326;
Angew. Chem. Int. Ed. 2011, 50, 5217-5220.
2
006, 71, 6291-6294; e) M. Black, J. I. G. Cadogan, H. McNab, Org.
Biomol. Chem. 2010, 8, 2961-2967; f) K. Li, A. Yu, X. Meng, Org. Lett.
018, 20, 1106-1109.
N. Arnau, M. Moreno-Manas, R. Pleixats, Tetrahedron 1993, 49, 11019-
1028.
For through S
Angew. Chem. 2010, 122, 4860-4864; Angew. Chem. Int. Ed. 2010, 49,
751-4754; b) T. H. Jepsen, M. Larsen, M. Jorgensen, K. A. Solanko, A.
12] a) T. Wesch, A. Berthelot-Bréhier, F. R. Leroux, F. Colobert, Org. Lett.
2013, 15, 2490-2493; b) P. Saravanan, P. Anbarasan, Org. Lett. 2014,
2
16, 848-851.
[
[
3]
4]
[
[
13] a) R. Che, Z. Wu, Z. Li, H. Xiang, X. Zhou, Chem. Eur. J. 2014, 20, 7258-
261; b) Q. Huang, S. Fu, S. Ke, H. Xiao, X. Zhang, S. Lin, Eur. J. Org.
1
7
N
Ar mechanism, see: a) M. Kienle, A. Unsinn, P. Knochel,
Chem. 2015, 6602-6605.
14] M. Tobisu, Y. Masuya, K. Baba, N. Chatani, Chem. Sci. 2016, 7, 2587-
4
2591.
D. Bond, A. Kadziola, M. B. Nielsen, Eur. J. Org. Chem. 2011, 53-57; c)
X. Shang, W. Chen, Y. Yao, Synlett 2013, 24, 851-854.
[
[
15] K. Nishino, Y. Ogiwara, N. Sakai, Eur. J. Org. Chem. 2017, 5892-5895.
16] R. Jira, In Applied Homogeneous Catalysis with Organometallic
Compounds; B. Cornils, W. A. Herrmann, Eds., Wiley-VCH: New York,
[
[
5]
6]
E
For through S Ar mechanism, see: a) H. Sirringhaus, R. H. Friend, C.
Wang, J. Leuninger, K. Müllen, J. Mater. Chem. 1999, 9, 2095-2101; b)
V. B. Pandya, M. R. Jain, B. V. Chaugule, J. S. Patel, B. M. Paemer, J.
K. Joshi, P. R. Patel, Synth. Commun. 2012, 42, 497-505.
2002; Vol. 1, p 386.
[
[
2
17] Instead of DMSO, when using an organic oxidant, PhI(OAc) (1.5 equiv),
the yield of 2a remarkably decreased to 14% yield.
a) M. Shimizu, M. Ogawa, T. Tamagawa, R. Shigitani, M. Nakatani, Y.
Nakano, Eur. J. Org. Chem. 2016, 2785-2788; b) M. Wang, Q. Fan, X.
Jiang, Org. Lett. 2016, 18, 5756-5759; c) M. Wang, J. Wei, Q. Fan, X.
Jiang, Chem. Commun. 2017, 53, 2918-2921; d) L. Liu, J. Qiang, S. Bai,
Y. Li, J. Li, Appl Organometal Chem. 2017, 31, e3810.
18] For examples that a Se-Se bond of diaryl diselenides is cleaved by
oxidative addition of a palladium(II) catalyst, see: a) A. J. Canty, H. Jin,
B. W. Skelton, A. H. White, Inorg. Chem. 1998, 37, 3975-3981; b) A. J.
Canty, M. C. Denney, J. Patel, H. Sun, B. W. Skelton, A. H. White, J.
Organomet. Chem. 2004, 689, 672-677.
[
7]
8]
Selected examples: a) L.-C. Campeau, P. Thansandote, K. Fagnou, Org.
Lett. 2005, 7, 2857-1860; b) B. Xiao, T.-J. Gong, Z.-J. Liu, J.-H. Liu, D.-
F. Luo, J. Xu, L. Liu, J. Am. Chem. Soc. 2011, 133, 9250-9253; c) Y. Wei,
N. Yoshikai, Org. Lett. 2011, 13, 5504-5507; d) H. Xu, L.-L. Fan, Chem.
Pharm. Bull. 2008, 56, 1496-1498; e) S. Maetani, T. Fukuyama, I. Ryu,
Org. Lett. 2013, 15, 2754-2757; f) N. Panda, I. Mattan, D. K. Nayak, J.
Org. Chem. 2015, 80, 6590-6597.
[
19] For an example of oxidation of a palladium(0) to a palladium(II) with
DMSO, see: W. C. P. Tsang, R. H. Munday, G. Brasche, N. Zheng, S. L.
Buchwald, J. Org. Chem. 2008, 73, 7603-7610.
[
20] For examples of preparation of benzo[b]thiophenes through a similar
reaction mechanism, see: a) K. Inamoto, Y. Arai, K. Hiroya, T. Doi, Chem.
Commun. 2008, 43, 5529-5531; b) A. Acharya, S. V. Kumar, H. Ila, Chem.
Eur. J. 2015, 21, 17116-17125.
[
Selected examples: a) W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am.
Chem. Soc. 2005, 127, 14560-14561; b) M. Yamamoto, S. Matsubara,
This article is protected by copyright. All rights reserved.