Iodine(<scp>i</scp>)-based and iodine(<scp>iii</scp>)-based halogen bond catalysis on the Friedel–Crafts reaction: a theoretical study

Zhao, Chang; Liu, Ying; Li, Xiaoyan; Zeng, Yanli

doi:10.1039/d3cp02541a

Cited by 4 publications

(8 citation statements)

References 65 publications

(88 reference statements)

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“…For XB catalysis, the Δ G values have linear relationships with ρ b values at bond critical points (BCPs) of iodine(III) XB, and the integral charges of region 2 were linear with the ρ b values at the BCPs of the iodine(III) XB. Thus, stronger XBs led to lower Δ G values, and stronger polarization further favors XB catalysis (Figure b, c) . Recently, the Kokotos research group used NHISs to study the Friedel–Crafts reaction between indole and aldehydes, and experimentally proved the XB interaction between NHISs and aldehydes, indicating the XB catalytic role played by NHIS in the reaction …”

Section: Halogen Bond Catalysismentioning

confidence: 91%

“…Thus, stronger XBs led to lower ΔG values, and stronger polarization further favors XB catalysis (Figure 3b, 3c). 52 Recently, the Kokotos research group used NHISs to study the Friedel−Crafts reaction between indole and aldehydes, and experimentally proved the XB interaction between NHISs and aldehydes, indicating the XB catalytic role played by NHIS in the reaction. 53 In addition, the Nazarov cyclization reaction (Scheme 7) is also a kind of organic reaction that can use XB donors as catalysts to activate divinyl ketones to cyclopentenone derivatives.…”

Section: Halogen Bond Catalysis On Carbonyl Complexesmentioning

confidence: 99%

“…(c) The relationship of ρ b values and integral charge values of region 2 catalyzed by iodine(III) catalysts. Adapted with permission from Figures 4, 5b, and 6b in ref . Copyright 2023 Royal Society of Chemistry.…”

Section: Halogen Bond Catalysismentioning

confidence: 99%

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Halogen Bond Catalysis: A Physical Chemistry Perspective

Li,

Zhao,

Wang

et al. 2024

J. Phys. Chem. A

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Section: Halogen Bond Catalysismentioning

confidence: 91%

Section: Halogen Bond Catalysis On Carbonyl Complexesmentioning

confidence: 99%

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Halogen Bond Catalysis: A Physical Chemistry Perspective

Li,

Zhao,

Wang

et al. 2024

J. Phys. Chem. A

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“…In 2019, Toy et al proposed an alternative approach for the Friedel–Crafts reaction of aldehydes and ketones with indole [ 93 – 94 ]. Bidentate halogen-bond donors are efficient catalysts, since they can form two halogen bonds with each substrate, instead of just one.…”

Section: Reviewmentioning

confidence: 99%

“…With catalyst 26 prepared, its use was then studied as a halogen-bond donor in the catalytic synthesis of 28 ( Scheme 11 ) [ 93 – 94 ]. Having identified the optimum reaction conditions, the general applicability was studied by reacting various indoles with a range of aldehydes and ketones to produce a wide range of bis(indolyl)methanes 28 in good to excellent yields (62–93%) [ 93 – 94 ].…”

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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Carbon–Bromide Bond Activation by Bidentate Halogen, Chalcogen, Pnicogen, and Tetrel Bonds

Yang,

Zhao,

Sun

et al. 2024

J. Phys. Chem. A

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Halogen, chalcogen, pnictogen, and tetrel bonds in organocatalysis have gained noticeable attention. In this work, carbon−bromide bond activation in the Ritter reaction by bidentate imidazole-type halogen, chalcogen, pnicogen, and tetrel bond donors was studied by density functional theory. All of the above four kinds of catalysts exhibited excellent catalytic performance. σ-hole interactions were formed between the Br atom of the reactant and the halogen, chalcogen, pnicogen, and tetrel bond donors, which elongated the C−Br bond and caused the rearrangement of the electron density of the precomplexes, resulting in the breaking of the C− Br bond and Br abstraction. Notably, the catalytic activity of the chalcogen bond is the best, followed by that of the halogen bond. Although the catalytic activity of pnicogen and tetrel bond catalysts is not as good as that of the halogen bond and chalcogen bond, they can still be used as effective substitutes for the halogen bond and chalcogen bond, providing more choices for noncovalent catalysis. Furthermore, within the same group, the fifth-period atomic catalyst is more effective than the fourth-period one for halogen, chalcogen, pnicogen, and tetrel bond donor catalysts.

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Iodine(i)-based and iodine(iii)-based halogen bond catalysis on the Friedel–Crafts reaction: a theoretical study

Abstract: Halogen bond catalysis, especially iodine derivatives catalysis, has attracted increasing attention in recent years due to the advantages of relatively cheap, stable, green, easy to handle and favorable catalytic activity....

Cited by 4 publications

References 65 publications

Halogen Bond Catalysis: A Physical Chemistry Perspective

Halogen Bond Catalysis: A Physical Chemistry Perspective

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

Carbon–Bromide Bond Activation by Bidentate Halogen, Chalcogen, Pnicogen, and Tetrel Bonds

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