Straight access to highly fluorescent angular indolocarbazoles via merging Au- and Mo-catalysis
- Suárez-Pantiga, Samuel 1
- Tapia, M. José 1
- Martínez-Lara, Fernando 1
- Suárez, Anisley 1
- Sanz, Roberto 1
- 1 Departamento de Química, Facultad de Ciencias, Universidad de Burgos
ISSN: 2052-4129
Año de publicación: 2020
Tipo: Artículo
Otras publicaciones en: Organic Chemistry Frontiers
Resumen
A straightforward and efficient synthesis of the two less explored types of indolocarbazoles has been developed giving rise to highly fluorescent compounds with fluorescence quantum yields around 0.7.
Referencias bibliográficas
- Sánchez, (2006), Nat. Prod. Rep., 23, pp. 1007, 10.1039/B601930G
- Olano, (2009), Mar. Drugs, 7, pp. 210, 10.3390/md7020210
- Nakano, (2009), J. Antibiot., 62, pp. 17, 10.1038/ja.2008.4
- Wang, (2018), J. Nat. Prod., 81, pp. 949, 10.1021/acs.jnatprod.7b01058
- Lai, (2015), Adv. Funct. Mater., 25, pp. 5548, 10.1002/adfm.201502079
- Gómez-Bombarelli, (2016), Nat. Mater., 15, pp. 1120, 10.1038/nmat4717
- Janosik, (2008), Tetrahedron, 64, pp. 9159, 10.1016/j.tet.2008.06.101
- Janosik, (2018), Chem. Rev., 118, pp. 9058, 10.1021/acs.chemrev.8b00186
- Tomlinson, (1951), J. Chem. Soc., pp. 809, 10.1039/JR9510000809
- Hall, (1953), J. Chem. Soc., pp. 116, 10.1039/JR9530000116
- Meragelman, (2002), J. Org. Chem., 67, pp. 6671, 10.1021/jo020120k
- Weller, (1983), J. Am. Chem. Soc., 105, pp. 6268, 10.1021/ja00358a014
- Desarbre, (1998), J. Chem. Soc., Perkin Trans. 1, pp. 2009, 10.1039/a802852d
- Bergman, (2000), Tetrahedron, 56, pp. 1911, 10.1016/S0040-4020(00)00100-9
- Suzuki, (2013), Chem. Lett., 42, pp. 1001, 10.1246/cl.130388
- Suzuki, (2014), Chem. – Asian J., 9, pp. 1841, 10.1002/asia.201402394
- Ihn, (2017), Adv. Sci., 4, pp. 1600502, 10.1002/advs.201600502
- Daniels, (2018), Eur. J. Org. Chem., pp. 4683, 10.1002/ejoc.201800791
- de Jong, (2019), J. Phys. Chem. B, 123, pp. 1400, 10.1021/acs.jpcb.8b10942
- Janoszik, (1999), Tetrahedron, 55, pp. 2371, 10.1016/S0040-4020(99)00030-7
- Wahlström, (2004), Tetrahedron Lett., 45, pp. 7273, 10.1016/j.tetlet.2004.08.024
- Nair, (2008), Org. Biomol. Chem., 6, pp. 1738, 10.1039/b803009j
- Dupeyre, (2011), Org. Biomol. Chem., 9, pp. 7780, 10.1039/c1ob06108a
- Zheng, (2014), Org. Lett., 16, pp. 5156, 10.1021/ol5025053
- Yang, (2016), Beilstein J. Org. Chem., 12, pp. 2490, 10.3762/bjoc.12.243
- Viji, (2012), Tetrahedron, 68, pp. 2453, 10.1016/j.tet.2012.01.070
- Nagase, (2013), Org. Biomol. Chem., 11, pp. 1456, 10.1039/c3ob27407a
- Carvajal-Miranda, (2016), J. Heterocycl. Chem., 53, pp. 762, 10.1002/jhet.2333
- Sankar, (2017), J. Org. Chem., 82, pp. 13583, 10.1021/acs.joc.7b01813
- Kawada, (2018), Chem. Sci., 9, pp. 8416, 10.1039/C8SC03525C
- Roy, (2012), Tetrahedron, 68, pp. 6099, 10.1016/j.tet.2012.05.007
- Schmidt, (2012), Chem. Rev., 112, pp. 3193, 10.1021/cr200447s
- Aggarwal, (2019), Org. Biomol. Chem., 17, pp. 8330, 10.1039/C9OB01381D
- Chen, (2016), Org. Lett., 18, pp. 5384, 10.1021/acs.orglett.6b02762
- Guo, (2016), Chem. – Eur. J., 22, pp. 18343, 10.1002/chem.201604317
- Huang, (2016), Org. Lett., 18, pp. 6200, 10.1021/acs.orglett.6b03257
- Wang, (2017), Org. Lett., 19, pp. 6140, 10.1021/acs.orglett.7b03021
- Choi, (2017), Chem. Commun., 53, pp. 3481, 10.1039/C7CC00103G
- Zhou, (2017), Chem. Commun., 53, pp. 6343, 10.1039/C7CC02808C
- Gu, (2018), Org. Lett., 20, pp. 4285, 10.1021/acs.orglett.8b01707
- Kundu, (2019), J. Org. Chem., 84, pp. 16003, 10.1021/acs.joc.9b02474
- Qiu, (2012), Org. Lett., 14, pp. 6198, 10.1021/ol3029498
- Zhang, (2013), Chem. – Eur. J., 19, pp. 10625, 10.1002/chem.201301203
- Qiu, (2014), Chem. – Eur. J., 20, pp. 14589, 10.1002/chem.201404769
- Alcaide, (2015), ACS Catal., 5, pp. 3417, 10.1021/acscatal.5b00471
- James, (2015), Org. Lett., 17, pp. 4372, 10.1021/acs.orglett.5b02216
- Zhou, (2017), Chem. Commun., 53, pp. 4722, 10.1039/C7CC00352H
- Fukuda, (1991), J. Org. Chem., 56, pp. 3729, 10.1021/jo00011a058
- Hashmi, (2000), Angew. Chem., Int. Ed., 39, pp. 2285, 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO;2-F
- Hashmi, (2000), J. Am. Chem. Soc., 122, pp. 11553, 10.1021/ja005570d
- Hashmi, (2007), Chem. Rev., 107, pp. 3180, 10.1021/cr000436x
- Corma, (2011), Chem. Rev., 111, pp. 1657, 10.1021/cr100414u
- Dorel, (2015), Chem. Rev., 115, pp. 9028, 10.1021/cr500691k
- Suárez, (2017), ChemistrySelect, 2, pp. 787, 10.1002/slct.201700013
- Liang, (2010), Angew. Chem., Int. Ed., 49, pp. 9734, 10.1002/anie.201004778
- Liang, (2016), RSC Adv., 6, pp. 29020, 10.1039/C6RA03321K
- Chalotra, (2018), J. Org. Chem., 83, pp. 14443, 10.1021/acs.joc.8b02193
- Turnu, (2019), Org. Lett., 21, pp. 7329, 10.1021/acs.orglett.9b02617
- Suárez, (2017), Org. Lett., 19, pp. 5074, 10.1021/acs.orglett.7b02303
- Yaragorla, (2018), ACS Omega, 3, pp. 15024, 10.1021/acsomega.8b02393
- Huang, (2016), Org. Lett., 18, pp. 6200, 10.1021/acs.orglett.6b03257
- Ranjani, (2019), Org. Lett., 21, pp. 675, 10.1021/acs.orglett.8b03848
- Sanz, (2007), Adv. Synth. Catal., 349, pp. 713, 10.1002/adsc.200600384
- Borrero, (2015), Org. Lett., 17, pp. 1754, 10.1021/acs.orglett.5b00528
- Yamamoto, (2017), Adv. Synth. Catal., 359, pp. 1747, 10.1002/adsc.201700122
- Kang, (2018), Eur. J. Med. Chem., 143, pp. 426, 10.1016/j.ejmech.2017.11.057
- García, (2016), Green Chem., 18, pp. 2335, 10.1039/C5GC02862K
- Rubio-Presa, (2017), Adv. Synth. Catal., 359, pp. 1752, 10.1002/adsc.201700071
- Rubio-Presa, (2017), Org. Lett., 19, pp. 5470, 10.1021/acs.orglett.7b02792
- Hernández-Ruiz, (2018), Synthesis, 50, pp. 4019, 10.1055/s-0037-1610236
- Rubio-Presa, (2018), Adv. Synth. Catal., 360, pp. 2216, 10.1002/adsc.201800278
- Suárez-Pantiga, (2019), Angew. Chem., Int. Ed., 58, pp. 2129, 10.1002/anie.201812806
- Hashmi, (2011), Angew. Chem., Int. Ed., 50, pp. 5762, 10.1002/anie.201100989
- Hashmi, (2012), Adv. Synth. Catal., 354, pp. 1273, 10.1002/adsc.201200092
- Hashmi, (2012), Chem. – Eur. J., 18, pp. 6576, 10.1002/chem.201200314
- Hashmi, (2012), Chem. – Eur. J., 18, pp. 10480, 10.1002/chem.201200306
- Hashmi, (2010), Angew. Chem., Int. Ed., 49, pp. 5232, 10.1002/anie.200907078
- J. R.Lakowicz , Principles of Fluorescence Spectroscopy , Springer , Baltimore , 2006
Los documentos del portal se actualizan diariamente. Esta fecha hace referencia a la actualización de la información relacionada con la estructura del portal (personas, grupos de investigación, unidades organizativas, proyectos...).