Synthesis of 6- and 7-Arylindoles<i>via</i>Palladium-Catalyzed Cross-Coupling of 6- and 7-Bromoindole with Arylboronic Acids

Carrera, George M.; Sheppard, George S.

doi:10.1055/s-1994-22752

Cited by 60 publications

(16 citation statements)

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“…The reaction can be easily scaled-up and many examples are reported in the literature. [62][63][64][65] It is worth noting that the reactivity of Grignard reagents towards nitro and nitrosoarenes is much higher than that of many carbonyl functions, such that the reagent is completely consumed in the indole formation before having a chance to attack any other reactive moiety. 58,66,67 Thus, only few very highly reactive electrophilic functions on the starting nitroarene need protection, in particular aldehyde and hydroxyl moieties.…”

Section: Monica Nardimentioning

confidence: 99%

Applications of Bartoli indole synthesis

2014

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In 1989, the reaction of vinyl magnesium halides with ortho-substituted nitroarenes leading to indoles was discovered. This reaction is now frequently reported as the "Bartoli reaction" or the "Bartoli indole synthesis" (BIS). It has rapidly become the shortest and most flexible route to 7-substituted indoles, because the classical indole syntheses generally fail in their preparation. The flexibility of the Bartoli reaction is great as it can be extended to heteroaromatic nitro derivatives and can be run on solid support. This review will focus on the use of the Bartoli indole synthesis as the key step in preparations of complex indoles, which appeared in the literature in the last few years.

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Section: Monica Nardimentioning

confidence: 99%

Applications of Bartoli indole synthesis

2014

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“…[1][2][3][4][5][6] Consequently, a sizable portion of recent US patents reports on organic process development of aromatic heterocycles. [7,8] A useful synthetic tool for the modification of such compounds is the SuzukiMiyaura coupling, [9,10] which has been applied for the preparation of arylpyridines, [11,12] bipyridines, [11][12][13][14][15] arylpyrimidines, [16][17][18] pyridopyridines [11,12,[19][20][21] and aryltriazines, [22,23] the synthesis of nucleosides [24,25] or the introduction of thiophene, [26,27] benzothiazole [28] or indolyl [29][30][31][32] moieties. Nonetheless, the cross-coupling chemistry of heterocyclic substrates suffers from limitations.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design

Fleckenstein

Plenio

2008

Chemistry A European J

121

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A dicyclohexyl(2-sulfo-9-(3-(4-sulfophenyl)propyl)-9H-fluoren-9-yl)phosphonium salt was synthesized in 64% overall yield in three steps from simple commercially available starting materials. The highly water-soluble catalyst obtained from the corresponding phosphine and [Na(2)PdCl(4)] enabled the Suzuki coupling of a broad variety of N- and S-heterocyclic substrates. Chloropyridines (-quinolines) and aryl chlorides were coupled with aryl-, pyridine- or indoleboronic acids in quantitative yields in water/n-butanol solvent mixtures in the presence of 0.005-0.05 mol % of Pd catalyst at 100 degrees C, chloropurines were quantitatively Suzuki coupled in the presence of 0.5 mol % of catalyst, and S-heterocyclic aryl chlorides and aryl- or 3-pyridylboronic acids required 0.01-0.05 mol % Pd catalyst for full conversion. The key to the high activity of the Pd-phosphine catalyst is the rational design of the reaction parameters (i.e., the presence of water in the reaction mixture, good solubility of reactants and catalyst in n-butanol/water (3:1), and the electron-rich and sterically demanding nature of the phosphine ligand).

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“…It was found that the 2‐arylindole‐3‐acetamide derivative (VI) was a FPP‐competitive inhibitor of farnesyl protein transferase [4f] . In this context, a variety of refined methods have emerged for the synthesis of indoles, including Fisher indole synthesis, [5a] Gassman indole synthesis, [5b] Bischler indole synthesis, [5c] Batcho‐Leimgruber synthesis, [5d] Larock indole synthesis [5e] and so on [5f] . Despite these milestones, chemists have never stopped their ambitions for pursuing the ideal synthesis and functionalization of indole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

2020

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The use of clean and renewable light sources is increasingly common in organic synthesis due to its safety, practicality and economy. Recently, photoredox catalysis has shown great application values in organic transformations because of its advantages of environmentally friendly and abundant resources. Indoles and their derivatives (indolines, oxindoles and isatins) are the core skeletons of some important organic compounds and widely‐present in various natural products and pharmaceuticals with different biological activities. Therefore, the research on the synthesis and modification of indoles is particularly important for chemists and pharmacologists. This review summarizes the effects of photocatalysis on indole synthesis and modification in recent decades. These transformations are accomplished by using metal photocatalysts (i. e., Ir, Ru, Ni, Cu, Fe, Au, Rh, TiO2, etc.) or non‐metallic photocatalysts (i. e., Rose Bengal, Eosin Y, quinones, naphthols, N‐heterocyclic carbenes, carbazoles, pyrylium salts, etc.), or without the need of photocatalysts. The detailed mechanisms of these photo‐catalyzed/promoted organic reactions are also highlighted deeply. And we hope this review will be helpful to researchers interested in this promising field of photocatalyzed transformations.

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Synthesis of 6- and 7-ArylindolesviaPalladium-Catalyzed Cross-Coupling of 6- and 7-Bromoindole with Arylboronic Acids

Cited by 60 publications

References 0 publications

Applications of Bartoli indole synthesis

Applications of Bartoli indole synthesis

Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

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