A Novel and Efficient Oxidation of Benzyl Alcohols to Benzaldehydes with DMSO Catalyzed by Acids.

Li, Chunbao; Xü, Yanli; Lu, Mang; Zhao, Zhenzhen; Liu, Lanjun; Zhao, Zheyuan; Cui, Yi; Zheng, Pengwu; Ji, Xioujie; Gao, Guangjie

doi:10.1002/chin.200309058

Cited by 2 publications

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“…On the other hand, the thiamin-catalyzed cyanide-free benzoin condensation of benzoate 5 gave more reproducible results, producing the desired α-hydroxyketone 6 in good yield [28]. Acid-catalyzed oxidation of compound 6 with DMSO gave the desired dicarbonyl intermediate 7 in quantitative yield [29,35]. Condensation of 7 with diamine 8 in dry ethanol afforded TPz 9 with high yield, followed by a DA with bromide 2, carrying the donor group, while quantitative ester hydrolysis under basic conditions allowed us to isolate dye TP2 in 83% yield.…”

Section: Synthesis Of the Dyesmentioning

confidence: 99%

Exploring Different Designs in Thieno[3,4-b]pyrazine-Based Dyes to Enhance Divergent Optical Properties in Dye-Sensitized Solar Cells

et al. 2023

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Two novel organic sensitizers for Dye-Sensitized Solar Cells (DSSC), called TP1 and TP2, based on the electron-poor thieno[3,4-b]pyrazine (TPz) π-bridge and the electron-rich N,N-bis(4-(hexylthio)phenyl)aniline (TPA) were designed following two different approaches: the classical D-A-π-A design and a symmetric structure with double anchoring functions. Both compounds were prepared exploiting short synthetic pathways based on direct arylation strategies and possibly one-pot desymmetrization. The two novel dyes displayed opposite optical properties: a broad and intense light absorption over the entire visible spectrum for TP1, and a localized absorption that peaked in the center of the visible region for TP2, resulting in a pitch-dark coloration and a green tone, respectively. When assembling the photovoltaic devices, different electrolyte compositions were explored to enhance the optical properties of the dyes. Power conversion efficiencies as high as 5.2% under full sun intensity were recorded for small test devices. The composition of the light transmitted through the TP2-containing transparent DSSC fits well with the human eye sensitivity spectrum, thus fulfilling the transparency requirements for building-integrated photovoltaics (BIPV).

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Section: Synthesis Of the Dyesmentioning

confidence: 99%

Exploring Different Designs in Thieno[3,4-b]pyrazine-Based Dyes to Enhance Divergent Optical Properties in Dye-Sensitized Solar Cells

et al. 2023

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“…On the other hand the complexes [Ir IV Cl 5 (RN(H)N=O)] •might also cleave hydroxide OHyielding diazonium radical complexes [Ir IV Cl 5 (RNN)] • which oxidise organic species and finally decompose to N 2 and solvent complexes [Ir III Cl 5 (L)] 2-.2.4 Reaction of the nitrosamine complexes [IrCl 5 (RN(H)N=O)] 2with acids 9The decomposition of [IrCl 5 (RN(H)N=O)]2From this it is clear that the combination of DMSO and strong acids has acted as oxidant of the nitrosamine complexes [Ir III Cl 5 (RN(H)N=O)] 2-. This is not unexpected since the so-called "activated" DMSO (Me 2 S + -Oor Me 2 S + -OE, with "E" being an electrophile) has been identified as oxidant in several studies showing that trifluoroacetic acid other acids are activating agents 31,32.…”

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confidence: 93%

Synthesis and structural characterisation of unprecedented primary N-nitrosamines coordinated to iridium(iv)

et al. 2018

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The redox chemistry of the N-nitrosamine complexes [IrCl5(RN(H)N[double bond, length as m-dash]O)]2- (R = benzyl or n-butyl) was studied in detail. One-electron oxidations at around 200 mV vs. ferrocene/ferrocenium were reversible in cyclic voltammograms. UV-vis spectroelectrochemistry reveals spectra characteristic of IrIV species but also partial decomposition of the oxidised species [IrIVCl5(RN(H)N[double bond, length as m-dash]O)]˙- on this timescale (minutes). Detailed studies on chemically oxidised solutions of the parent IrIII complexes gave evidence for paramagnetic IrIV from NMR spectra. Final products of the decomposition were the corresponding alcohols and presumably [IrIIICl5(L)]2- (L = N2, solvent, amine) complexes. Similar decomposition reactions of acidic DMSO solutions of [IrCl5(RN(H)N[double bond, length as m-dash]O)]2-revealed that this combination produces the so-called "activated" DMSO (Me2S+-O- or Me2S+-OE, with "E" being an electrophile) which oxidises the parent IrIII complexes. Finally, with the very reactive purple IrIV compound (PPh4)[IrCl5(BnN(H)N[double bond, length as m-dash]O)], the first primary N-nitrosamine coordinated to [IrIVCl5]- was isolated and characterised by UV-vis absorption, FTIR, NMR spectroscopy, ultra-high resolution electrospray mass spectrometry (UHR-ESI-MS) and iridium L3 X-ray absorption near-edge spectroscopy (XANES).

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A Novel and Efficient Oxidation of Benzyl Alcohols to Benzaldehydes with DMSO Catalyzed by Acids.

Cited by 2 publications

References 1 publication

Exploring Different Designs in Thieno[3,4-b]pyrazine-Based Dyes to Enhance Divergent Optical Properties in Dye-Sensitized Solar Cells

Exploring Different Designs in Thieno[3,4-b]pyrazine-Based Dyes to Enhance Divergent Optical Properties in Dye-Sensitized Solar Cells

Synthesis and structural characterisation of unprecedented primary N-nitrosamines coordinated to iridium(iv)

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