18
(a) N. Jeelan Basha, S. M. Basavarajaiah and K. Shyamsunder,
Mol. Divers., 2022, 26, 2915–2937; (b) T. Fukuda, F. Ishibashi
and M. Iwao, in The Alkaloids: Chemistry and Biology, ed. H.-J.
Knölker, Academic Press, 2020, vol. 83, pp. 1–112; (c) Y. Ding,
Y. Tang, W. Zhu and Y. Xie, Chem. Soc. Rev., 2015, 44, 1101–
1112.
For a recent review, see: S. C. Philkhana, F. O. Badmus, I. C.
Dos Reis and R. Kartika, Synthesis, 2021, 53, 1531–1555.
For selected recent examples, see: (a) H. C. Chiu and I. A.
Tonks, Angew. Chem. Int. Ed., 2018, 57, 6090–6094; (b) A.
Kondoh, A. Iino, S. Ishikawa, T. Aoki and M. Terada, Chem. Eur.
J., 2018, 24, 15246–15253; (c) P. K. Mishra, S. Verma, M.
Kumar and A. K. Verma, Org. Lett., 2018, 20, 7182–7185; (d)
B. Prabagar, R. K. Mallick, R. Prasad, V. Gandon and A. K.
Sahoo, Angew. Chem. Int. Ed., 2019, 58, 2365–2370; (e) J.-K.
Li, B. Zhou, Y.-C. Tian, C. Jia, X.-S. Xue, F.-G. Zhang and J.-A. Ma,
Org. Lett., 2020, 22, 9585–9590.
For selected reviews, see: (a) L. I. Belen'kii, T. G. Kim, I. A.
Suslov and N. D. Chuvylkin, Russ. Chem. Bull., 2005, 54, 853–
863; (b) B. Borah, K. D. Dwivedi and L. R. Chowhan, Asian J.
Org. Chem., 2021, 10, 2709–2762.
For selected examples via pyrrolyllithium species, see: (a) M.
G. Banwell, B. L. Flynn, E. Hamel and D. C. R. Hockless, Chem.
Commun., 1997, 207–208; (b) T. Fukuda, T. Ohta, E.-i. Sudo
and M. Iwao, Org. Lett., 2010, 12, 2734–2737.
For selected reviews, see: (a) J. F. Bunnett, Acc. Chem. Res.,
1972, 5, 139–147; (b) M. Schnürch, M. Spina, A. F. Khan, M. D.
Mihovilovic and P. Stanetty, Chem. Soc. Rev., 2007, 36, 1046–
1057; (c) W. Erb and F. Mongin, Tetrahedron, 2016, 72, 4973–
4988; (d) K. Inoue and K. Okano, Asian J. Org. Chem., 2020, 9,
1548–1561.
J. Fröhlich, Bull. Soc. Chim. Belg., 1996, 105, 615–634.
(a) S. Kano, Y. Yuasa, T. Yokomatsu and S. Shibuya,
Heterocycles, 1983, 20, 2035–2037; (b) H. Fröhlich and W. Kalt,
J. Org. Chem., 1990, 55, 2993–2995; (c) K. Okano, K. Sunahara,
Y. Yamane, Y. Hayashi and A. Mori, Chem. Eur. J., 2016, 22,
16450–16454.
(a) D. Morikawa, K. Morii, Y. Yasuda, A. Mori and K. Okano, J.
Org. Chem., 2020, 85, 8603–8617; (b) K. Morii, Y. Yasuda, D.
Morikawa, A. Mori and K. Okano, J. Org. Chem., 2021, 86,
13388–13401; (c) Y. Okui, Y. Yasuda, A. Mori and K. Okano,
Synthesis, 2022, 54, 2647–2660.
To the best of our knowledge, there are no reported examples
of 2,5-dibromothiophene undergoing the halogen dance to
provide 2,3-dibromothiophene derivatives.
(a) J.-H. Liu, Q.-C. Yang, T. C. W. Mak and H. N. C. Wong, J. Org.
Chem., 2000, 65, 3587–3595; (b) B. Jolicoeur, E. E. Chapman,
A. Thompson and W. D. Lubell, Tetrahedron, 2006, 62, 11531–
11563; (c) W. Ishiga, M. Ohta, T. Kodama and M. Tobisu, Org.
Lett., 2021, 23, 6714–6718.
L. Jones and B. J. Whitaker, J. Comput. Chem., 2016, 37, 1697–
1703.
In the case of N-trisyl-2,3-dibromopyrrole 3g, the use of 3
mol% tribromopyrrole 6g did not promote isomerization of
3g' to 2g'.
The structures of compounds 7a and 8a were determined by
HMBC experiments.
The structures of compounds 7b and 8b were determined by
NOE experiments.
Recently, Bandar and co-workers have reported that
brominated or iodinated thiophenes could be used as a
halogen-transfer reagent for synthesizing a series of Nheteroaryl halides: T. R. Puleo, D. R. Klaus and J. S. Bandar, J.
Am. Chem. Soc., 2021, 143, 12480–12486.
B. D. Roth, in Progress in Medicinal Chemistry, eds. F. D. King,
A. W. Oxford, A. B. Reitz and S. L. Dax, Elsevier, 2002, vol. 40,
pp. 1–22.
T. J. Donohoe, N. J. Race, J. F. Bower and C. K. A. Callens, Org.
Lett., 2010, 12, 4094–4097.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins
...