A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid

Liu, Jiao; Yin, Shan; Wang, Haimei; Li, Hongfang; Ni, Guanghui

doi:10.1016/j.carres.2020.107963

Cited by 13 publications

(5 citation statements)

References 18 publications

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“…Excitingly, 1a showed no signs of decomposition under these conditions, and the reaction proceeded to 38% conversion of 2a after 20 h. However, the significant deceleration of the reaction progression after 12 h, and the high price and low availability of Ir(ppy) 2 (dtbpy)PF 6 , prompted us to investigate more cost-effective organic photocatalysts, using commercially available LED light sources (Table , entries 2–13). Fluorescein derivative Eosin Y was able to activate SF 6 to form 2a in low conversions (Table , entry 2). A related dye, Rose Bengal, was also tested, but it did not show any catalytic activity (Table , entry 3).…”

mentioning

confidence: 99%

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

et al. 2020

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This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%−97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

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confidence: 99%

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

et al. 2020

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“…Continuing in the same array, Ni et al published visible light-mediated glycosylation en route to Oglycosides in the presence of eosin Y as an organophotoacid in DCM as a solvent (Scheme 41). [106] Scheme 38. A plausible mechanism of photoacid catalyzed glycosylation.…”

Section: Eosin Y As Photoredox Catalystmentioning

confidence: 99%

Recent Advances and Development in Visible‐Light‐Mediated Glycosylation: An Expanding Research Area in Glycochemistry

Azeem

Mandal

2023

Adv Synth Catal

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In the last fifteen years, the development of visible‐light photocatalysis, metal/photoredox dual catalysis has become the forefront as a new paradigm in organic synthesis as well as in carbohydrate chemistry. It led to the discovery of unprecedented transformations and also the improvement of known reactions under mild conditions, employing simple household light sources and bench‐stable precursors, which meet the requirements of green chemistry and sustainable development in excellent yield and stereocontrol. In a general sense, the exploitation of photoredox catalysis hinges on the capability of photocatalyst or redox mediator to transform visible light into chemical energy via photo‐irradiated SET (single electron transfer), PET (photoinduced electron transfer), HAT (hydrogen atom transfer), and XAT (halogen atom transfer) to potentially unlock unique reaction pathways, thereby generating a diverse array of reactive intermediates. In view of reaction type, mechanism, and status, this review will systematically summarize the latest advances in visible‐light‐promoted photocatalytic glycosylation reactions, which are driven by single or dual photoredox catalysis and by the photoactivity of electron donor‐acceptor (EDA) complexes.

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“…In a subsequent report, Ni and co-workers showed that irradiation of 20 mol% eosin Y (5) with visible light, 450 nm LEDs, also facilitates the glycosylation of alcohols with -glycosyl trichloroacetimidates, although the /-selectivity is low (: ≈ 1:1). 21 The Wang Group has shown that photoirradiation of 1 mol% 5 in combination with 2 mol% diphenyl disulfide (19) additive, facilitates the -stereoselective synthesis of 2-deoxyglycosides 21 from a variety of protected glycal donors 20 with a range of alcohol acceptors (Scheme 7). [22][23][24] Importantly, the unique mild reactivity of this photoacid-catalyzed protocol avoids the competitive formation of Ferrier-type side products 22, which result from facile elimination of C3-acyl protected glycals.…”

Section: Short Review Synthesis 3 Glycosylationmentioning

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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A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid

Cited by 13 publications

References 18 publications

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

Recent Advances and Development in Visible‐Light‐Mediated Glycosylation: An Expanding Research Area in Glycochemistry

Recent Advances in Photoacid Catalysis for Organic Synthesis

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