A convenient iodination of indoles and derivatives

Hamri, Salha; Rodríguez, José María Barragán; Basset, Joan; Guillaumet, Gérald; Pujol, Maria Dolors

doi:10.1016/j.tet.2012.05.053

Cited by 15 publications

(7 citation statements)

References 36 publications

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“…According to the general procedure, 7-azaindole (70.9 mg, 0.6 mmol), bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 μmol), and DIH (171.0 mg, 0.45 mmol) were reacted in acetonitrile (2 mL) for 1 h to afford 2s (138.6 mg, 95% yield), which was purified by flash column chromatography (hexane/AcOEt = 3:1) as a pale yellow solid: 1 H NMR (500 MHz, CDCl 3 ) δ = 8.34 (d, J = 4.9 Hz, 1H), 7.77 (d, J = 8.1 Hz, 1H), 7.43 (s, 1H), 7.18 (dd, J = 8.1, 4.9 Hz, 1H). The NMR spectrum was identical to that previously reported …”

Section: Methodssupporting

confidence: 83%

“…The NMR spectrum was identical to that previously reported. 54 5-Bromo-3-iodo-1H-indazole (2t). According to the general procedure, 5-bromo-1H-indazole (118.2 mg, 0.6 mmol), bis(4methoxyphenyl) disulfide 3c (1.7 mg, 6 μmol), and DIH (171.0 mg, 0.45 mmol) were reacted in acetonitrile (2 mL) for 19 h to afford 2s (89.4 mg, 46% yield), which was purified by flash column chromatography (hexane/AcOEt = 4:1) as a white solid: 1 H NMR (400 MHz, DMSO-d 6 ) δ = 13.70 (s, 1H), 7.60 (s, 1H), 7.54−7.53 (m, 1H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Iida

Ishida

Watanabe³

et al. 2019

J. Org. Chem.

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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

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Section: Methodssupporting

confidence: 83%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Iida

Ishida

Watanabe³

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

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“…There would be several other advantages: (1) Strong oxidants (e.g., Br 2 ), toxic mercury salts 23 and/or the more difficult to prepare and use alkenylboronic acids 24 [vs. B(pin) derivatives] would not be needed. (2) Severely basic conditions for (pin)B-to-halogen exchange and reactive halide sources (e.g., iodine monochloride), which may be detrimental to certain functionality (e.g., sulfides 25 or indoles 26 ), would not be necessary. (3) Product purification would be more practical: organic halide reagents are more easily removable (sufficiently volatile) and do not afford pinacol byproduct that can be difficult to separate from the desired product.…”

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confidence: 99%

Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis

Koh

Nguyen

Zhang

et al. 2016

Nature

167

117

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Olefin metathesis has made a significant impact on modern organic chemistry, but important shortcomings remain: for example, the lack of efficient processes that can be used to generate acyclic alkenyl halides. Halo-substituted ruthenium carbene complexes decompose rapidly or deliver low activity and/or minimal stereoselectivity, and our understanding of the corresponding high-oxidation-state systems is very limited. In this manuscript, we show that previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of an in situ-generated catalyst with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents and proceed to high conversion at ambient temperature within four hours. Many alkenyl chlorides, bromides and fluorides can be obtained in up to 91 percent yield and complete Z selectivity. This method can be used to easily synthesize biologically active compounds and to perform the site- and stereoselective fluorination of other organic compounds.

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“…Recently, new reports about effective, mild and safe iodination procedures emerged for arenes (Espuña et al 2004;Barluenga et al 2007;Racys et al 2016) and heterocycles (Barluenga et al 1993;Hamri et al 2012;Przypis and Walczak 2019). In this subject, hypervalent iodine reagents have been at the forefront of synthetic methodology developments in the past 20 years (Merritt and Olofsson 2009;Yoshimura and Zhdankin 2016).…”

Section: Introductionmentioning

confidence: 99%

“…In this subject, hypervalent iodine reagents have been at the forefront of synthetic methodology developments in the past 20 years (Merritt and Olofsson 2009;Yoshimura and Zhdankin 2016). Multiple examples of iodonium salt usage in organic synthesis have been reported in recent literature (Barluenga et al 1993;Espuña et al 2004;Hamri et al 2012;Borzenko et al 2015;Racys et al 2016;Iskra and Murphree 2017;Liu et al 2017;Przypis and Walczak 2019). Aryliodonium and diaryliodonium salts play a special role in this field because they are air-and moisture stable and soluble in many organic solvents despite their reactive framework.…”

Section: Introductionmentioning

confidence: 99%

Convenient but powerful method to dope single-walled carbon nanotube films with iodonium salts

et al. 2019

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Single-walled carbon nanotubes (SWCNTs) demonstrate unique properties of both electrical and thermal conductivity, but at the moment of producing a network composed of multiple nanotubes, these values sharply decrease. It is associated with the presence of defects in the nanotube network structure, as well as with the dissipation phenomena at the junctions between SWCNTs. One of the methods to alleviate this problem is doping. In our study, we obtained a film made of high-quality SWCNTs doped with three types of iodonium salts: Barluenga's reagent (bispyridineiodonium tetrafluoroborate, IPy 2 BF 4), pyridine iodine monochloride (IPyCl) and diphenyliodonium chloride (DPIC). We recorded a significant improvement in electrical properties after doping with IPy 2 BF 4 and IPyCl, by as much as 224% and 322%, respectively. What is more, we noted improvement in thermal conductivity, which amounted to over 50% when the material was doped with IPyCl. Our research indicates that permanent doping of CNT-based ensembles is possible with iodonium salts. The process significantly improves electrical conductivity, and the compounds themselves are more convenient to work with rather than when other halogen-based dopants are used commonly for this purpose.

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A convenient iodination of indoles and derivatives

Cited by 15 publications

References 36 publications

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis

Convenient but powerful method to dope single-walled carbon nanotube films with iodonium salts

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