Iron-catalyzed C(sp3)–H phosphorylation via photoinduced LMCT

Liu, Hongchi; Wang, Kaifang; Ye, Sunfeng; Zhu, Qiming; Huang, Hanmin

doi:10.1039/d3qo02121a

Org. Chem. Front.

2024

DOI: 10.1039/d3qo02121a

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Iron-catalyzed C(sp³)–H phosphorylation via photoinduced LMCT

Hongchi Liu,

Kaifang Wang,

Sunfeng Ye

et al.

Abstract: Alkylphosphines demonstrate excellent performance as ligands, catalysts and reagents based on their strong electron-donating properties. However, current methods for synthesizing alkylphosphines are limited to nucleophilic substitution reactions of air-sensitive organometallic...

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Cited by 7 publications

References 51 publications

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C(sp³)−H Functionalization Using Chlorine Radicals

Sadeghi

2024

Adv Synth Catal

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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.

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C(sp³)−H Functionalization Using Chlorine Radicals

Sadeghi

2024

Adv Synth Catal

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Recent progress in metal-catalyzed C(sp³)-P bond formation

Tu,

Shen,

Huang

2024

Tetrahedron

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Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling

Yang,

Wu,

et al. 2024

Org. Lett.

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Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R 2 PCl), which forms a fragile C�N−O−PR 2 species that undergoes N−O homolysis, fragmentation, and radical−radical coupling, leading to the formation of cyano-containing phosphine oxides in good yields. The reaction features an in situ activation of cyclobutanone oximes for radical generation, in which R 2 PCl plays a dual role as both an activator and a reactant.

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Iron-catalyzed C(sp³)–H phosphorylation via photoinduced LMCT

Abstract: Alkylphosphines demonstrate excellent performance as ligands, catalysts and reagents based on their strong electron-donating properties. However, current methods for synthesizing alkylphosphines are limited to nucleophilic substitution reactions of air-sensitive organometallic...

Cited by 7 publications

References 51 publications

C(sp³)−H Functionalization Using Chlorine Radicals

C(sp³)−H Functionalization Using Chlorine Radicals

Recent progress in metal-catalyzed C(sp³)-P bond formation

Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling

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Iron-catalyzed C(sp3)–H phosphorylation via photoinduced LMCT

Abstract: Alkylphosphines demonstrate excellent performance as ligands, catalysts and reagents based on their strong electron-donating properties. However, current methods for synthesizing alkylphosphines are limited to nucleophilic substitution reactions of air-sensitive organometallic...

Cited by 7 publications

References 51 publications

C(sp3)−H Functionalization Using Chlorine Radicals

C(sp3)−H Functionalization Using Chlorine Radicals

Recent progress in metal-catalyzed C(sp³)-P bond formation

Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling

Contact Info

Product

Resources

About

Iron-catalyzed C(sp³)–H phosphorylation via photoinduced LMCT

C(sp³)−H Functionalization Using Chlorine Radicals

C(sp³)−H Functionalization Using Chlorine Radicals