Excited-State Palladium-Catalyzed Radical Migratory Mizoroki–Heck Reaction Enables C2-Alkenylation of Carbohydrates

Yao, Wang; Zhao, Gaoyuan; Wu, Yangjie; Zhou, Ling; Mukherjee, Upasana; Liu, Peng; Ngai, Ming‐Yu

doi:10.1021/jacs.1c13299

Cited by 54 publications

(40 citation statements)

References 65 publications

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“…The same authors have also recently reported the application of this strategy to a Mizoroki‐Heck reaction to achieve the C‐ 2‐selective alkenylation of carbohydrates [69] …”

Section: Deoxygenative C−h Bond Formationmentioning

confidence: 99%

“…This exists in equilibrium between species 88, where the Pd is directly bonded to C-1 (forming a covalently bonded Pd II The same authors have also recently reported the application of this strategy to a Mizoroki-Heck reaction to achieve the C-2-selective alkenylation of carbohydrates. [69]…”

Section: Via Photochemistrymentioning

confidence: 99%

“…Saccharides and nucleosides are fundamental biomolecules possessing several hydroxy groups, thus representing ideal targets for the application of late stage deoxyfunctionalisation strategies. Although some advancements have been made in this area, [68][69]82] there is still a lack of general methodologies that can be applied for selective nucleoside derivatisations.…”

Section: Selective Saccharide and Nucleoside Derivatisationsmentioning

confidence: 99%

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Radical Deoxyfunctionalisation Strategies**

et al. 2022

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Due to their abundance and readily available synthesis, alcohols provide ideal handles for the selective derivatisation of organic molecules. Radical chemistry offers versatile strategies for the conversion of Csp3−O bonds into a wide range of Csp3−C, Csp3−H, or Csp3−heteroatom bonds. In these reactions, alcohols are readily derivatised with an activator group which can undergo facile mesolysis to generate a primary, secondary, or tertiary open‐shell species that can engage in further transformations. These strategies are particularly effective at overcoming steric limitations associated with nucleophilic substitution pathways. Despite their potential, the use of radical deoxyfunctionalisation reactions as a general strategy for the synthesis of useful and complex molecules remains underutilised. In this Review, we highlight recent advancements in this exciting field in which photocatalysis, transition metal catalysis or electrochemistry are used to initiate the radical processes.

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“…The same authors have also recently reported the application of this strategy to a Mizoroki‐Heck reaction to achieve the C‐ 2‐selective alkenylation of carbohydrates [69] …”

Section: Deoxygenative C−h Bond Formationmentioning

confidence: 99%

Section: Via Photochemistrymentioning

confidence: 99%

Section: Selective Saccharide and Nucleoside Derivatisationsmentioning

confidence: 99%

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Radical Deoxyfunctionalisation Strategies**

et al. 2022

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“…The same authors have also recently reported the application of this strategy to a Mizoroki-Heck reaction to achieve the C2-selective alkenylation of carbohydrates. [56] [Ir(ppy) 2 (dtbbpy)]PF 6 (2 mol%) blue LEDs (λ max = 455 nm) H 2 O (100 equiv.)…”

Section: Scheme 31 Deoxygenation Of Benzylic Alcohols Via B-scissionmentioning

confidence: 99%

“…Saccharide and nucleosides are fundamental biomolecules possessing several hydroxy groups, thus representing ideal targets for the application of late-stage deoxyfunctionalisation strategies. Although some advancements have been made in this area, [55][56]69] there is still a lack of general methodologies that can be applied for selective nucleoside derivatisations. We believe that at the current pace of innovation, these challenges will be tackled in the not-so-distant future.…”

Section: ) Selective Saccharide and Nucleoside Derivatisationsmentioning

confidence: 99%

Radical Deoxyfunctionalisation Strategies

Anwar

Merkens

Troyano

et al. 2022

Preprint

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Due to their abundance and readily available synthesis, alcohols provide ideal handles for the selective derivatisation of organic molecules. Radical chemistry offers versatile strategies for the conversion of Csp3–O bonds into a wide range of Csp3–C or Csp3–heteroatom bonds. In these reactions, alcohols are readily derivatised with an activator group which can undergo facile mesolysis to generate a primary, secondary, or tertiary open-shell species that can engage in further transformations. These strategies are particularly effective at overcoming steric limitations associated with nucleophilic substitution pathways. Despite their potential, the use of radical deoxyfunctionalisation reactions as a general strategy for the synthesis of useful and complex molecules remains underutilised. Herein, we highlight recent advancements in this exciting field using photocatalysis, transition metal catalysis or electrochemistry to initiate the radical processes.

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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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Excited-State Palladium-Catalyzed Radical Migratory Mizoroki–Heck Reaction Enables C2-Alkenylation of Carbohydrates

Cited by 54 publications

References 65 publications

Radical Deoxyfunctionalisation Strategies**

Radical Deoxyfunctionalisation Strategies**

Radical Deoxyfunctionalisation Strategies

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

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