Green chemistry: efficient acetalization of aldehydes with alcohols using the acid red 52 photocatalyst

Yu, Linyu; Lin, Chuyuan; Liao, Chunshu; Zeng, Xianghua; Chen, Xiuwen; Zhu, Zhongzhi; Huang, Yubing; Li, Yibiao; Lu, Chunmei

doi:10.1007/s10311-020-00994-y

Cited by 14 publications

(5 citation statements)

References 33 publications

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“…To address the important point concerning the effectiveness of HNTT as a photo‐driven proton releasing system, we have employed HNTT as photocatalyst in the reaction of acetalization of aldheydes with alcohols, which has been recently shown to be effectively promoted under photoacidic conditions [41–46] . The results are summarized in Figure 3, where the conversion yields for benzaldehyde and 3‐phenylpropionaldehyde are reported.…”

Section: Resultsmentioning

confidence: 99%

“…To address the important point concerning the effectiveness of HNTT as a photo-driven proton releasing system, we have employed HNTT as photocatalyst in the reaction of acetalization of aldheydes with alcohols, which has been recently shown to be effectively promoted under photoacidic conditions. [41][42][43][44][45][46] The results are summarized in Figure 3, where the conversion yields for benzaldehyde and 3-phenylpropionaldehyde are reported. Inspection of Figure 3 shows that a mixture of HNTT (5 % mol) and 3-phenylpropionaldehyde in acetonitrile/methanol (3 : 2) irradiated at 365 nm resulted in total conversion to the corresponding acetal within 2.5 hours.…”

Section: Chemphotochemmentioning

confidence: 99%

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High N‐H Photoacidity of a Nitrogen‐Rich Fused Ring Heteroaromatic Scaffold

et al. 2022

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It is shown that 4-methyl-7-(4-nitrophenyl)-triazolo[3,2-c]triazole exhibits a high photoacidity, unprecedented in neutral molecules in which the proton is delivered by a NH bond, which promotes acetalization of aldehydes under irradiation by a near-UV low power LED. Time dependent transient absorption spectroscopy shows a series of stimulated emission signals attributable to photo-tautomerization and formation of the deprotonated species, followed by broad positive absorption band which does not decay within the investigated timescale, compatible with the formation of a long living species, possibly the anion in the lowest energy triplet state. Computational analyses qualitatively confirm the strong photoacidity of the molecule in all its tautomeric forms, allow to assign transient absorption signals, and show that the first singlet excited state exhibits high spin-orbit couplings with excited triplet states which could promote a fast singlet-triplet transition, thus leading to a long living species able to photocatalyze chemical reactions.

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Section: Resultsmentioning

confidence: 99%

Section: Chemphotochemmentioning

confidence: 99%

High N‐H Photoacidity of a Nitrogen‐Rich Fused Ring Heteroaromatic Scaffold

et al. 2022

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“…1). 4–6 In this report we show that using visible light irradiation, 6-bromo-2-naphthol ( 3 ) functions as a photoacid catalyst for the synthesis of acetals. 7,8 We also demonstrate that photosensitization of 2-naphthol in the presence of a photosensitizer facilitates the acetalization of electron-deficient aldehydes.…”

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confidence: 85%

Photoacid-catalyzed acetalization of carbonyls with alcohols

2022

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“…Additional acetalization reactions involving a catalytically generated photoacidic radical cation includes work done in 2004 by Lijser and co-workers, when irradiat-ed with 350 or 420 nm light in protic media catalytic chloranil (64) forms in situ photoacid catalyst TCHQ (2,3,5,6-tetrachloro-1,4-hydroquinone) and work by Chen and coworkers using the organophotoacid 65 (Scheme 12, B). 31,32…”

Section: Short Review Synthesis 4 Acetalizationmentioning

confidence: 99%

Recent Advances in Photoacid Catalysis for Organic Synthesis

Saway¹,

Salem²,

Badillo³

2020

Synthesis

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Photoacids are molecules that become more acidic upon the absorption of light. This short review highlights recent advances in the use of photoacids as catalysts for organic synthesis. Photoacid-catalyzed transformations discussed herein include: Protonation, glycosylation, acetalization, and arylation reactions.1 Introduction2 Protonation: Excited-State Proton Transfer (ESPT)3 Glycosylation4 Acetalization5 Friedel–Crafts Arylation6 Additional C–C and C–S Bond-Forming Reactions7 Conclusion

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Green chemistry: efficient acetalization of aldehydes with alcohols using the acid red 52 photocatalyst

Cited by 14 publications

References 33 publications

High N‐H Photoacidity of a Nitrogen‐Rich Fused Ring Heteroaromatic Scaffold

High N‐H Photoacidity of a Nitrogen‐Rich Fused Ring Heteroaromatic Scaffold

Photoacid-catalyzed acetalization of carbonyls with alcohols

Recent Advances in Photoacid Catalysis for Organic Synthesis

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