FeCl3-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical

Yang, Yingying; He, Na; Huang, Xinxiang; Song, Xizhong; Chen, Jingbo; Jiang, Lin; Jing, Yi

doi:10.1039/d3cc03186a

Chem. Commun.

2023

DOI: 10.1039/d3cc03186a

|View full text |Cite

FeCl₃-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical

Yingying Yang

Na He

Xinxiang Huang

et al.

Abstract: Herein, we report the development of iron-catalyzed benzylic C−H oxidative amidation reactions via photoinduced ligand-to-metal charge transfer (LMCT). These reactions exhibit broad substrate scope (60 examples) and offer operationally simple,...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 7 publications

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

C(sp³)−H Functionalization Using Chlorine Radicals

Sadeghi

2024

Adv Synth Catal

View full text Add to dashboard Cite

Converting any desired C‐H bond to the intended C‐Z bond in a given organic molecule could be the final peak of the C‐H functionalization methodology. Among the three types of C‐H bonds, the functionalization of the ubiquitous C(sp3)‐H bond has gained special attention, especially in the last two decades. There are different ways to transform a C(sp3)‐H bonds to desired C‐Z bonds and using chlorine radicals is one of them with a bright future. The literature review shows different sources have been used for chlorine including chloride anion (from HCl or salts), coordinated chlorine (from transition metal complex), and organic chlorides (from organochlorine compounds), although, HCl and FeCl3 have gained the most attention among them. There are three major ways to convert chlorine from these sources to chlorine radicals: 1) the oxidation of hydrogen chloride or chloride salts, 2) the photolysis of metal chloride, and 3) the transition metal insertion into C‐Cl bonds. This review aims to summarise published research papers about using chlorine radicals for C(sp3)‐H bonds functionalization and do not participate in the products as the substitutions for hydrogens. Therefore, the chlorination reaction of C(sp3)‐H bonds and the reactions in which chlorine radicals do not play a direct role in C(sp3)‐H bond breaking are not the subject of this review.

show abstract

C(sp³)−H Functionalization Using Chlorine Radicals

Sadeghi

2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Green Synthesis of Quinazolinones via Selective Electro‐oxidation Using Iron Electrode and NaCl Electrolyte as an Eco‐friendly Electrolyte

Basem,

Naglah,

Alaridhee

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Primary alcohols 2(a–h) and o‐aminobenzamides 1(a–h) can be selectively oxidized electrochemically to yield dihydroquinazolinone 4(a–h) and quinazolinones 5(a–h) in an efficient and chemoselective manner. This methodology employs sodium chloride (NaCl) 3(a) as a co‐catalyst and electricity as the oxidizing agent, utilizing cost‐effective and commercially available materials such as Graphite anode, Iron (Fe) cathode, and isopropyl alcohol (iPrOH) as a solvent and weak base. The synthesis yields various quinazolinone derivatives with diverse structural characteristics in good quantities, showcasing the method‘s broad applicability. This approach facilitates the production of a range of dihydroquinazolinones and quinazolinones (24 examples), highlighting its versatility and compatibility with different functional groups. Characterization of the synthesized derivatives included CHN analysis, 1HNMR spectroscopy, and determination of melting points.

show abstract

CuO Decorated Magnetic Reduced Graphene Oxide Catalyzed Cross-Dehydrogenative Coupling of Thiols and Alkylbenzenes

Rousta,

Khalili,

Ebrahimi

et al. 2024

Catal Lett

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

FeCl₃-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical

Abstract: Herein, we report the development of iron-catalyzed benzylic C−H oxidative amidation reactions via photoinduced ligand-to-metal charge transfer (LMCT). These reactions exhibit broad substrate scope (60 examples) and offer operationally simple,...

Cited by 7 publications

References 32 publications

C(sp³)−H Functionalization Using Chlorine Radicals

C(sp³)−H Functionalization Using Chlorine Radicals

Green Synthesis of Quinazolinones via Selective Electro‐oxidation Using Iron Electrode and NaCl Electrolyte as an Eco‐friendly Electrolyte

CuO Decorated Magnetic Reduced Graphene Oxide Catalyzed Cross-Dehydrogenative Coupling of Thiols and Alkylbenzenes

Contact Info

Product

Resources

About

FeCl3-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical

Abstract: Herein, we report the development of iron-catalyzed benzylic C−H oxidative amidation reactions via photoinduced ligand-to-metal charge transfer (LMCT). These reactions exhibit broad substrate scope (60 examples) and offer operationally simple,...

Cited by 7 publications

References 32 publications

C(sp3)−H Functionalization Using Chlorine Radicals

C(sp3)−H Functionalization Using Chlorine Radicals

Green Synthesis of Quinazolinones via Selective Electro‐oxidation Using Iron Electrode and NaCl Electrolyte as an Eco‐friendly Electrolyte

CuO Decorated Magnetic Reduced Graphene Oxide Catalyzed Cross-Dehydrogenative Coupling of Thiols and Alkylbenzenes

Contact Info

Product

Resources

About

FeCl₃-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical

C(sp³)−H Functionalization Using Chlorine Radicals

C(sp³)−H Functionalization Using Chlorine Radicals