A simple, efficient and green procedure for the synthesis of bis-indolyl methanes in 1,1,1,3,3,3-hexafluoro-2-propanol

Khaksar, Samad; Talesh, Saeed Mohammadzadeh

doi:10.1016/j.jfluchem.2011.09.001

Cited by 25 publications

(8 citation statements)

References 49 publications

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“…A protocol for the synthesis of substituted bis(indolyl)methanes was developed using the condensation of indole or N -methylindole with diverse aldehydes in HFIP at rt; the reaction in TFE proceeded slowly and gave poorer yields (Scheme ). The authors also demonstrated the recovery of HFIP in excellent purity for reuse over three cycles without affecting yields.…”

Section: C–c Bond-forming Reactionsmentioning

confidence: 97%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: C–c Bond-forming Reactionsmentioning

confidence: 97%

HFIP in Organic Synthesis

et al. 2022

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“…In 2012, Khaksar and co-workers introduced an efficient and simple synthetic protocol which employed 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as both the catalyst and solvent of the reaction ( Scheme 74 ) [ 206 ]. HFIP has served in various organic transformations as a hydrogen-bond donor, which rendered it as a strong candidate for the synthesis of BIMs.…”

Section: Reviewmentioning

confidence: 99%

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Kolagkis,

Galathri,

Kokotos

2024

Beilstein J. Org. Chem.

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The synthesis of indoles and their derivatives, more specifically bis(indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti-inflammatory, and even anticancer agents. Traditionally, the synthesis of BIMs has been achieved upon the acidic condensation of an aldehyde with indole, utilizing a variety of protic or Lewis acids. However, due to the increased environmental awareness of our society, the focus has shifted towards the development of greener synthetic technologies, like photocatalysis, organocatalysis, the use of nanocatalysts, microwave irradiation, ball milling, continuous flow, and many more. Thus, in this review, we summarize the medicinal properties of BIMs and the developed BIM synthetic protocols, utilizing the reaction between aldehydes with indoles, while focusing on the more environmentally friendly methods developed over the years.

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“…The optimization experiments revealed that the highest yield (98%) was attained when solvent-free conditions were used in the model reaction ( Table 5, Entry 9). Then, the impact of temperature on the completion of the reaction was evaluated ( [72] (Continues) [70] 10 H H 90 123-126 124-125 [73] 11 H H 92 101-103 100-102 [68] 12 H H 92 201-204 201-203 [70] 13 H H 89 192-195 194 [74] 14 CH 3 H 6 93 249-252 250-253 [43] 15 CH 3 H 5 97 240-242 241-243 [43] observed that the maximum yield was obtained when 90 C temperature was used when performing the reaction under solvent-free conditions ( Table 5, Entry 9). Decreasing the temperature caused a smaller yield of the desired product (Table 5, Entries 6-8), while increasing the temperature required for the reaction to 120 C did not affect the reaction time and the product yield ( Table 5, Entries 10-12).…”

Section: Transmission Electron Microscopy Analysis Of So 3 H@fe 3 Omentioning

confidence: 99%

Heterogeneous SO₃H@Fe₃O₄ magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives

Peng

2020

J Chinese Chemical Soc

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This work aimed to synthesize a new heterogeneous catalyst (SO 3 H@Fe 3 O 4 magnetic nanoparticles) and the study of its catalytic behavior in synthesizing 3,3 0-(arylmethylene)-bis-(4-hydroxycoumarin), bis-(indolyl)-methane, and 1,8-dioxo-octahydroxanthene derivatives. The characterization of obtained material has been performed by means of Fourier-transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, vibrating sample magnetometer, and transmission electron microscopy. The main properties of this new methodology, compared to earlier ones, are the short times of reaction, mild reaction conditions, simple recovery of the catalyst by permanent magnetic field, excellent yields, and reusability of the catalyst for a minimum of six runs.

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A simple, efficient and green procedure for the synthesis of bis-indolyl methanes in 1,1,1,3,3,3-hexafluoro-2-propanol

Cited by 25 publications

References 49 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Heterogeneous SO₃H@Fe₃O₄ magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives

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A simple, efficient and green procedure for the synthesis of bis-indolyl methanes in 1,1,1,3,3,3-hexafluoro-2-propanol

Cited by 25 publications

References 49 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Heterogeneous SO3H@Fe3O4 magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives

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Heterogeneous SO₃H@Fe₃O₄ magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives