Green Molecular Transformation in Dual Catalysis: Photoredox Activation of Vitamin B12 Using Heterogeneous Photocatalyst DOI Creative Commons
Keita Shichijo, Hisashi Shimakoshi

ChemPlusChem, Journal Year: 2024, Volume and Issue: 89(6)

Published: Feb. 22, 2024

Abstract This concept focuses on dual‐catalysis using metal complexes and heterogeneous photocatalysts. Vitamin B 12 derivatives are sophisticated that facilitate enzymatic reactions in the biological systems. The enzymes inspired catalytically proceed dual‐catalyst systems of photocatalysts, such as titanium oxide (TiO 2 ) metal‐organic frameworks (MOFs), under light irradiation. cobalt ions effectively reduced by photoexcited producing low‐valent Co(I) species. photoinduced nucleophilic species react with an alkyl halide to form organometallic complex a Co−C bond. bond dissociates during photolysis generate radicals. Based this mechanism, promotes various light‐driven organic syntheses dehalogenation toxic halides. trends system recent progress field discussed concept.

Language: Английский

Nitrocyclopropanes as Valuable Building Blocks in Organic Synthesis and Biology: Exploring the Origin of the Nitro Group DOI Creative Commons
Andriani G. Chaidali, Michael A. Terzidis, Ioannis N. Lykakis

et al.

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 30, 2025

Cyclopropane derivatives serve as important building blocks in organic synthesis, due to their three-membered stretched ring. Nitro-substituted cyclopropanes (NCPs) represent a special class of donor-acceptor (DACs) that contain strong electron-withdrawing nitro group substituent on the cyclopropyl moiety. Due versatile nature group, which can be converted into other functional azo groups or heterocyclic scaffolds, NCPs are considered design complex compounds. Herein, present review is organized two main sections focused synthesis and application NCPs. The part containing synthetic methodologies has been further divided distinct based mainly starting materials, such as: a) from nitroalkenes, b) nitro-bearing diazo compounds, c) nitroalkanes combination with alkenes, d) aminocyclopropanes under oxidative conditions, e) various through miscellaneous processes. In concerning applications use NCPs, categorization includes three subcategories, reduction 1-aminocyclopropane-1-carboxylic acids (ACC), ring opening leading valuable open-chain heterocycles, expansion larger cyclic

Language: Английский

Citations

0

New reactivity of late 3d transition metal complexes in catalytic reactions of alkynes DOI
Shenghan Teng,

Peiyao Liang,

Jianrong Steve Zhou

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes seven types of new reactivities found in late 3d metal complexes and catalytic examples recent years.

Language: Английский

Citations

0

Enhancing Cyanocobalamin Stability through Polymer Cyclodextrins: A Comprehensive Review on light stability DOI

P. K. Kulkarni,

Venkatesh Venkatesh,

Kishore Joshi

et al.

Research Journal of Pharmacy and Technology, Journal Year: 2025, Volume and Issue: unknown, P. 907 - 911

Published: Feb. 27, 2025

Cyanocobalamin, an important form of vitamin B12, is significantly degraded when exposed to light, affecting its potency and effectiveness. In this review, we describe in detail the effectiveness polymeric cyclodextrins as protectants for cyanocobalamin, with a particular focus on their role enhancing photostability. This article summarizes recent advances explains mechanism by which protect cyanocobalamin from photodegradation. We explained structural properties cyclodextrin, encapsulation ability, synergistic interaction cyanocobalamin. Additionally, review evaluates different methods analytical techniques used assess photostability provide insight into practical implications pharmaceutical nutraceutical applications. By synthesizing current research results, will narrate how serve promising candidates preserving photosensitivity thereby demonstrate sustained efficacy various formulations. It aims comprehensive understanding what contributes applicability.

Language: Английский

Citations

0

Vitamin B12 Derivative Enables Cobalt-Catalyzed Atom Transfer Radical Polymerization DOI
Sajjad Dadashi‐Silab, Cristina Preston‐Herrera, Erin E. Stache

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(35), P. 19387 - 19395

Published: Aug. 22, 2023

Advances in controlled radical polymerizations by cobalt complexes have primarily taken advantage of the reactivity as a persistent to reversibly deactivate propagating chains forming carbon-cobalt bond. However, cobalt-mediated require stoichiometric ratios complex, deterring its utility synthesizing well-defined polymers. Here, we developed strategy use catalyst control via halogen atom transfer with alkyl halide initiators. Using modified, hydrophobic analogue vitamin B12 (heptamethyl ester cobyrinate) precatalyst, polymerization acrylate monomers. The efficiency was significantly improved additional bromide anions, which enhanced deactivation radicals yielding polymers dispersity values <1.2 using concentrations low 5 mol %. We anticipate that development catalysis will enable new opportunities designing catalytic systems for synthesis

Language: Английский

Citations

10

Visible-Light-Induced Iron Group Metal Catalysis: Recent Developments in Organic Synthesis DOI

Changzhen Yin,

Miao Wang,

Zhenxi Cai

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 54(22), P. 4864 - 4882

Published: Aug. 8, 2022

Abstract One central research goal for modern organic chemistry in society is to develop sustainable synthetic methodologies. Visible-light-induced transformations that apply earth-abundant metals as catalysts are a good reply this concern. In short review, recent developments of photocatalysis applying iron group metal (Fe, Co, Ni) discussed. Reaction types, the catalyst details, and mechanisms introduced. 1 Introduction 2 Visible-Light-Induced Fe-Catalyzed Reactions 3 Co-Catalyzed 4 Ni-Catalyzed 5 Summary

Language: Английский

Citations

13

Electrocatalytic Reduction of Disulfide Bonds in Antibodies DOI Creative Commons
Serge Ruccolo, Marion H. Emmert, Cecilia Bottecchia

et al.

Published: Feb. 19, 2024

In most FDA-approved antibody-drug conjugates, cysteines generated through reduction of the native interchain di-sulfide bonds in monoclonal antibodies (mAbs) are conjugated with maleimide-based cytotoxic payloads. Despite being key to efficiently producing well-defined selective disulfide strategies severely underdevel-oped. Herein, we report a vitamin B12-catalyzed, electrochemically driven protocol that reduces various aqueous buffers and at broad pH range. This robust simple method is suitable for reduc-tions substrates ranging from biologically relevant small molecules large proteins. Finally, one-pot reduc-tion/conjugation mAbs was achieved access antibody conjugates.

Language: Английский

Citations

2

Aqueous Micellar Environment Impacts the Co-Catalyzed Phototransformation: A Case Study DOI Creative Commons
Aleksandra Wincenciuk, Piotr Cmoch, Maciej Giedyk

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 19828 - 19838

Published: July 9, 2024

In recent years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve regio-, stereo-, and chemoselectivity different transformations. Herein, we demonstrate aqueous environment is a suitable for visible light driven cobalt-catalyzed involving radical species. this system, reduced vitamin B

Language: Английский

Citations

2

Electrocatalytic Reduction of Disulfide Bonds across Chemical Modalities DOI
Serge Ruccolo, Marion H. Emmert, Cecilia Bottecchia

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6169 - 6173

Published: July 12, 2024

The chemical properties of disulfides are leveraged in a wide array applications, ranging from protein-drug conjugates for cancer treatment to self-healing materials. However, disulfide reduction strategies remain severely underdeveloped despite being the key efficiently accessing desired targets. Specifically, no homogeneous catalyst has been reported this reaction, and conditions that allow use mild green reductants (e.g., via electrochemical reduction) not known. Herein, we unveil vitamin B

Language: Английский

Citations

2

Vitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening DOI Creative Commons

Brian E. Funk,

Martin Pauze, Yen‐Chu Lu

et al.

Cell Reports Physical Science, Journal Year: 2023, Volume and Issue: 4(4), P. 101372 - 101372

Published: April 1, 2023

Epoxide ring-opening reactions have long been utilized to furnish alcohol products that are valuable in many subfields of chemistry. While epoxide-opening known, the hydrogenative opening epoxides via ionic means remains challenging because harsh conditions and reactive hydride nucleophiles. Recent progress has shown radical chemistry can achieve epoxide ring under relatively mild conditions; however, these methods invariably require oxophilic metal catalysts sensitive reagents. In response challenges, we report a new approach hydrogenation using bio-inspired Earth-abundant vitamin B12 thiol-centric hydrogen atom transfer (HAT) co-catalysis produce Markovnikov alcohols visible light irradiation. This powerful reaction system exhibits broad substrate scope, including number electrophilic reductively labile functionalities would otherwise be susceptible reduction or cleavage by nucleophiles, preliminary mechanistic experiments consistent with process.

Language: Английский

Citations

5

Catalytic Applications of Vitamin-Supported Nanoparticles in Organic Chemistry DOI

Razieh Farsi,

Mehdi Fallah‐Mehrjardi, Seyyed Jafar Saghanezhad

et al.

Russian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 59(3), P. 503 - 520

Published: March 1, 2023

Language: Английский

Citations

4