Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(5), P. 3013 - 3032

Published: Feb. 18, 2022

Sulfones are common, readily available reagents that have recently attracted attention as versatile for cross-coupling reactions. This Review summarizes advances in desulfonylative transformations of sulfones affected by molecular catalysis, including transition-metal catalysts, photocatalysts, and organocatalysts. In addition to catalyst choice, the design sulfonyl group is a critical factor control reactivity. The concepts presented herein will provide new strategies construct diverse molecules with high efficiency modularity.

Language: Английский

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Iron-catalysed reductive cross-coupling of glycosyl radicals for the stereoselective synthesis of C-glycosides

Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(3), P. 235 - 244

Published: Feb. 17, 2022

Language: Английский

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Visible light activation enables desulfonylative cross-coupling of glycosyl sulfones

Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(12), P. 967 - 974

Published: Sept. 22, 2022

Language: Английский

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Direct synthesis of unprotected aryl C-glycosides by photoredox Ni-catalysed cross-coupling

Nature Synthesis, Journal Year: 2023, Volume and Issue: 2(3), P. 251 - 260

Published: Jan. 16, 2023

Language: Английский

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Diversification of Glycosyl Compounds via Glycosyl Radicals

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(38)

Published: June 7, 2023

Glycosyl radical functionalization is one of the central topics in synthetic carbohydrate chemistry. Recent advances metal-catalyzed cross-coupling chemistry and metallaphotoredox catalysis provided powerful platforms for glycosyl diversification. In particular, discovery new precursors conjunction with these advanced reaction technologies have significantly expanded space compound synthesis. this Review, we highlight most recent progress area starting from 2021, reports included will be categorized based on different types better clarity.

Language: Английский

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In vitro antioxidant and free-radical scavenging activities of polar leaf extracts of Vernonia amygdalina

BMC Complementary Medicine and Therapies, Journal Year: 2023, Volume and Issue: 23(1)

Published: May 4, 2023

Plants are able to deliver a huge number of differing bioactive compounds which may supplement the requirements human body by acting as natural antioxidants. Antioxidants mindful for defense component life form against pathologies related assault free radicals. The main purpose this study was investigate qualitative phytochemical composition Vernonia amygdalina leaf extract and its antioxidant activity.The powdered plant sample successively extracted with aqueous, methanol ethanol solvents using Soxhlet apparatus. activities crude were determined 1, 1- diphenyl-2-picryl hydrazyl (DPPH) radical, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) phosphomolybdate (PM) hydrogen peroxide (H2O2) scavenging assay. All examinations drained triplicates average values each test taken.Phytochemical investigation revealed that three solvent extracts contained numerous namely alkaloids, tannins, saponins, phenols, terpenoids, steroids, glycosides sugars. result showed that, V. obtained from exhibit maximum activity compared aqueous extracts. IC50 DPPH assay H2O, MeOH EtOH 111.4, 94.92 94.83 μg/ml; ABTS 334.3, 179.8 256.9 H2O2 141.6, 156 180.6 μg/ml, respectively. radical in while lowest method. data vitro models clearly suggest has higher due presence phenolic constituents extract.This noteworthy mitigating traditional use different aliments.

Language: Английский

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Radical Pathway Glycosylation Empowered by Bench-Stable Glycosyl Donors

Accounts of Chemical Research, Journal Year: 2023, Volume and Issue: 56(18), P. 2473 - 2488

Published: Aug. 18, 2023

ConspectusThe study of carbohydrates has emerged as a crucial research area in various disciplines due to their pivotal roles cellular processes. To facilitate in-depth exploration biological functions, chemical glycosylation reactions that allow facile access glycoconjugates broad community are highly needed. In classical reactions, glycosyl donor is activated by an acid generate reactive electrophilic intermediate, which subsequently forms glycosidic bond upon reaction with nucleophilic acceptor. Such ionic pathway been the mainstay technique for glycoconjugate synthesis and allowed numerous intricate structures. Nevertheless, limitations still exist. For instance, when labile donors or harsh activating conditions required, these methods show limited tolerance hydroxyl groups abundant on sugar rings. addition, achieving good stereocontrol represents another longstanding obstacle. recent years, new modes activation have sought tackle above challenges.We noted passing through intermediacy radicals via cascade single-electron transfer steps possess significant but underexplored potential. Progress this slow large part dearth handy maneuver radicals. Most existing call either forcing unstable/inconvenient starting materials. order better exploit power radical glycosylation, we developed range donors─namely, sulfoxides, sulfones, sulfinates─that bench stable can be readily prepared from simple These form under mild conditions. Enabled use donors, series could used making O-, S-, C-glycosides, some were previously difficult access. many cases, no protecting group required. As illustration potential utility, our adopted preparation sugar–drug conjugates, sugar–DNA glycopeptides, even glycoproteins. While most cases intrinsic reactivity intermediates explored axially configured products, also utilization external, delicate reagents, catalysts override such innate preference achieve catalyst-controlled stereoselectivity.We believe enormous inspire development novel glycoside synthesis. Account, highlight design principles summarize advancements enabled use, provide outlook future directions field.

Language: Английский

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Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry

Chemical Science, Journal Year: 2024, Volume and Issue: 15(4), P. 1204 - 1236

Published: Jan. 1, 2024

This review article highlights the diverse ways in which recent developments areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry.

Language: Английский

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N-glycoside synthesis through combined copper- and photoredox-catalysed N-glycosylation of N-nucleophiles

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(5), P. 623 - 632

Published: March 1, 2024

Language: Английский

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Nonenzymatic StereoselectiveS-Glycosylation of Polypeptides and Proteins

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(31), P. 11919 - 11926

Published: July 29, 2021

Here we report a nonenzymatic glycosylation reaction that builds axial S-glycosidic bonds under biorelevant conditions. This strategy is enabled by the design and use of allyl glycosyl sulfones as precursors to radicals exploits exceptional functional group tolerance radical processes. Our method introduces variety unprotected units cysteine residues peptides in highly selective fashion. Through developing second-generation protocol, applied our direct complex polypeptides proteins. Computational studies were performed elucidate mechanism.

Language: Английский

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