Silver-mediated radical phosphorylation/cyclization of <i>N</i>-allylbenzamides to access phosphoryl-substituted dihydroisoquinolones

Liu, Xiao‐Ceng; Sun, Kai; Lv, Qi‐Yan; Chen, Xiaolan; Sun, Yuanqiang; Peng, Yu‐Yu; Qu, Lingbo; Yu, Bing

doi:10.1039/c9nj02833a

Cited by 22 publications

(4 citation statements)

References 65 publications

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“…Later, Liu and co-workers reported a method for the efficient synthesis of a variety of phosphoryl-substituted dihydroisoquinolones from methacryloylbenzamides and P(O)H compounds via a silver-mediated reaction (Scheme 50). 58 Different silver salts and solvents were screened, and the results showed that AgNO 3 was the best oxidant and CH 3 CN was the most effective solvent. The amount of AgNO 3 was investigated, and the results indicated that 2 equivalents of silver salt were required in this reaction.…”

Section: Reviewmentioning

confidence: 99%

Recent developments in the synthesis of the isoquinoline-1,3(2H,4H)-dione by radical cascade reaction

Niu

Xia

2022

Org. Biomol. Chem.

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Section: Reviewmentioning

confidence: 99%

Recent developments in the synthesis of the isoquinoline-1,3(2H,4H)-dione by radical cascade reaction

Niu

Xia

2022

Org. Biomol. Chem.

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“…Although a pioneering radical amino-phosphorylation of unactivated alkenes of 2-allylanilines toward 2-phosphonomethyl-N-sulfonyl indolines has been established by Zhang et al [24] , the development of an economical method from readily available materials remains highly desirable. In 2018, Liang et al [25] developed a silver-catalyzed radical arylphosphorylation of unactivated alkenes via a cascade phosphorylation-arylation sequence [Figure 9]. This protocol displays a broad substrate scope, high exo/endo selectivity and simple operation, with a diverse array of 3-phosphonoalkyl indolines obtainable in satisfactory yields.…”

Section: Intramolecular Carbophosphorylationmentioning

confidence: 99%

Advances in radical phosphorylation from 2016 to 2021

Liu¹,

Xiao²,

Fu³

et al. 2021

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Organophosphorus compounds are of great significance in organic chemistry. Therefore, the construction of phosphorus-containing compounds has attracted significant attention from organic chemists. Radical phosphorylation has become a powerful strategy for building organophosphorus compounds and numerous achievements have been realized in recent years. In this review, we summarize the development of the generation and application of phosphorus radicals in organic chemistry since 2016. Special emphasis is given to various new transformations involving the generation of P-centered radicals via transition metal catalytic, photochemical and electrochemical means. Recent advances in the development of metal-free catalytic phosphorylations involving Pcentered radicals are also reviewed.

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“…A gram‐scale synthesis could also be readily carried out by the authors. One year later, Chen, Sun, Yu and co‐workers aslo developed similar phosphorylation/cyclization strategy between N ‐allylbenzamides with phosphine oxides to accomplish the phosphoryl‐substituted dihydroisoquinolones consturcted [34] . Compared with Liang's alkene substrates, they used the carbon chain growth substrates with one more carbon atom (Scheme 30).…”

Section: Silver‐mediated Two‐component Alkene Functionalization Reactmentioning

confidence: 99%

Recent Advances in Silver‐Mediated Radical Difunctionalization of Alkenes

Xiao

Yang

et al. 2020

ChemCatChem

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Radical‐initiated difunctionalization of alkenes is one of the most important methods in organic synthesis and medicinal chemistry, which can be applied to synthesize value complex compounds as well as structural motifs that found in bioactive natural products and pharmaceuticals. In recent years, impressive progress have been made in this area with ideal silver catalysis. Here, we summarize recent advances in silver‐mediated radical difunctionalization of alkenes for the formation of diverse bonds, including 1) two‐component radical difunctionalization reactions enabled by an intramolecular cyclization process toward various cyclic compounds and 2) three‐component radical difunctionalization reactions leading to complex linear compounds. These silver‐mediated radical alkene difunctionalization transformations are general initiated by different radicals, such as carbon‐, oxygen‐, sulfur‐, phosphinyl‐, and halogen‐center radicals, followed by terminated with nucleophiles to form two new bonds in a single reaction.

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Silver-mediated radical phosphorylation/cyclization of N-allylbenzamides to access phosphoryl-substituted dihydroisoquinolones

Abstract: A silver-mediated phosphorylation/cyclization of N-allylbenzamides with phosphine oxides for the synthesis of phosphoryl-substituted dihydroisoquinolones was developed.

Cited by 22 publications

References 65 publications

Recent developments in the synthesis of the isoquinoline-1,3(2H,4H)-dione by radical cascade reaction

Recent developments in the synthesis of the isoquinoline-1,3(2H,4H)-dione by radical cascade reaction

Advances in radical phosphorylation from 2016 to 2021

Recent Advances in Silver‐Mediated Radical Difunctionalization of Alkenes

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