2020
DOI: 10.1007/s41061-020-0287-7
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Recent Advances on the C2-Functionalization of Indole via Umpolung

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Cited by 39 publications
(14 citation statements)
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“…In this case, the C3-phenyl-substituted indole was obtained as the major product (C2/C3 = 10:90), but it was isolated in yield as low as 21% (Table , entry 1). This result confirmed the natural tendency of the process to yield the thermodynamically favored C3 product under thermal Pd-free conditions and also that both arylated indoles and the starting material are prone to some decomposition when the reaction is performed at high temperatures, due to the polymerization of indole moieties. , …”
Section: Resultssupporting
confidence: 71%
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“…In this case, the C3-phenyl-substituted indole was obtained as the major product (C2/C3 = 10:90), but it was isolated in yield as low as 21% (Table , entry 1). This result confirmed the natural tendency of the process to yield the thermodynamically favored C3 product under thermal Pd-free conditions and also that both arylated indoles and the starting material are prone to some decomposition when the reaction is performed at high temperatures, due to the polymerization of indole moieties. , …”
Section: Resultssupporting
confidence: 71%
“…Direct C–H functionalization of indoles is potentially of great synthetic utility, providing access to an important class of heterocyclic systems. In fact, an indole scaffold is considered as a privileged structure in medicinal chemistry, and it is present in a large number of natural products endowed with biological activity. …”
Section: Introductionmentioning
confidence: 99%
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“…As one of the most important heterocycles, indole is widely present in natural products and medicines due to its remarkable biological activity, such as antibacterial (Van Order and Lindwall., 1942;Bell et al, 1994), anti-obesity (Sashidhara et al, 2012), antimicrobial (Sivaprasad et al, 2006), vaginal spermicide (Paira et al, 2009), and apoptosis in acute myelogenous leukemia (AML) (Contractor et al, 2005). The functionalization of the indole core mainly occurs at the N1, C2, and C3 positions (Bandini and Eichholzer, 2009;Joucla and Djakovitch., 2009;Bartoli et al, 2010;Dalpozzo., 2015;Sandtorv., 2015;Deka et al, 2020). Among them, the C3 position modification of indoles is mainly achieved by transition metal-catalyzed C-H bond functionalization (Phipps et al, 2008;Leitch et al, 2017;Ye et al, 2020).…”
Section: Introductionmentioning
confidence: 99%
“…High-boiling neutral nitrogen compounds (HBNNCs), including carbazole and indole, which are mainly derived from anthracene and wash oil, have been widely applied in chemical and pharmaceutical industries for the production of medicines, , synthetic resins, , and pesticides . To date, generally in industry, HBNNCs are obtained from anthracene and wash oil by alkali fusion, acid washing, and volatile organic solvent extraction methods, which can lead to serious impacts on the environment.…”
Section: Introductionmentioning
confidence: 99%