Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases

Koradin, Christopher; Döhle, Wolfgang; Rodriguez, Alain L.; Schmid, Bertram; Knöchel, Paul

doi:10.1016/s0040-4020(03)00073-5

Cited by 251 publications

(125 citation statements)

References 86 publications

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“…All diynes 2a, [8] 2b, [8] 2c, [21] 2d, [22] 2e, [8] 2f, [23] 2g, [8] 2h, [24] 2i, [25] 2j, [8] 2k, [8] 2l, [26] 2m, [27] 2n, [10] 2o, [28] and 2p [29] were characterised by comparison of their physical and spectroscopic data with those described in the literature.…”

Section: /Kap1mentioning

confidence: 99%

Homocoupling of Terminal Alkynes Catalysed by Ultrafine Copper Nanoparticles on Titania

et al. 2011

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Section: /Kap1mentioning

confidence: 99%

Homocoupling of Terminal Alkynes Catalysed by Ultrafine Copper Nanoparticles on Titania

et al. 2011

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“…7). It is worth noting that the weakly polar toluene was employed as the solvent in our transformation, and the results significantly differ from those methods [42][43][44] using strongly polar solvents. 45 Based on these experiments and the relevant reports, 46 we tend to the opinion that the domino transformation probably underwent the intermolecular C-N coupling / intramolecular cyclization pathway (Eq.…”

Section: Methodsmentioning

confidence: 78%

“…2). [41][42][43][44] We attempted to capture the intermediate N-phenyl-2-(phenylethynyl)aniline 5a or 2-phenylindole 6a at a lower temperature (Eq. 3).…”

Section: Methodsmentioning

confidence: 99%

A practical Cu(I)-catalyzed domino approach to 1,2-disubstituted indoles and its application for the assembly of indolophenanthridines

Gao¹,

Xu²,

Shao³

et al. 2015

Arkivoc

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A facile and efficient approach to 1,2-disubstituted indoles has been developed using a novel Cu(I)-catalyzed cascade coupling/cyclization reaction of 2-alkynylanilines with aryl iodides. Facilitated by CuI/t-BuOK without any ligand or CuI/Cs 2 CO 3 /1,10-phenanthroline, a variety of 1,2-disubstituted indoles were conveniently generated in one pot with good to excellent yields. Furthermore, a series of indolo[1,2-f]phenanthridines were successfully assembled from the tandem reactions of 2-alkynylanilines with o-dihaloarenes through copper-catalyzed coupling / cyclization followed by palladium-catalyzed intramolecular direct C(sp 2 )-H arylation.

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“…Undec-5-en-1-yne 22 (Table 1, entry 6), p-(1-phenylethynyl)styrene 23 (entry 7) and 2-(phenylethynyl)aniline 24 (entry 12) were prepared according to reported procedures. (Table 1, entry 5).…”

Section: Substrates Synthesismentioning

confidence: 99%

Nickel phosphide nanocatalysts for the chemoselective hydrogenation of alkynes

et al. 2012

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Elsevier Carenco, S.; Leyva Perez, A.; Concepción Heydorn, P.; Boissiere, C.; Mezailles, N.; Corma Canós, A. (2012) Well-defined 25 nm nickel phosphide nanoparticles act as a colloidal catalyst for the chemoselective hydrogenation of terminal and internal alkynes. Cis-alkenes are obtained in mild conditions (85°C, a few hours) with good conversion and selectivity. The phosphorus inserted in the Ni-P nanoparticles is critical for the selectivity of the nanocatalyst. Mechanistic investigations support a pre-reduction of the catalyst for its activation. They pinpoint the occurrence of C-H bond cleavage in terminal alkynes during the reaction.

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Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases

Cited by 251 publications

References 86 publications

Homocoupling of Terminal Alkynes Catalysed by Ultrafine Copper Nanoparticles on Titania

Homocoupling of Terminal Alkynes Catalysed by Ultrafine Copper Nanoparticles on Titania

A practical Cu(I)-catalyzed domino approach to 1,2-disubstituted indoles and its application for the assembly of indolophenanthridines

Nickel phosphide nanocatalysts for the chemoselective hydrogenation of alkynes

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