Synthesis of (−)-Piperitylmagnolol Featuring <i>ortho</i>-Selective Deiodination and Pd-Catalyzed Allylation

N‐Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time‐efficient and general method for the iodination of a wide range of mono‐ and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono‐iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.

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“…GC–MS: m/z (%) = 220 (100) [M + ], 93, 65, 127, 110, 191. Spectroscopy data accords with the literature , …”

Section: Methodssupporting

confidence: 86%

N‐Iodosuccinimide (NIS) in Direct Aromatic Iodination

et al. 2017

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“…The preparation of diiodoanisole 8 from 2- tert -butylphenol proved to be straightforward (Scheme ). Treatment of 2- tert -butylphenol with NaI and bleach , proved an efficient method for installing the iodides in diiodophenol 13 . Methylation (NaOH, MeI, acetone) then completed the synthesis of diiodoanisole 8 .…”

Section: Resultsmentioning

confidence: 99%

Discovery and Development of Metal-Catalyzed Coupling Reactions in the Synthesis of Dasabuvir, an HCV-Polymerase Inhibitor

et al. 2019

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Dasabuvir (1) is an HCV polymerase inhibitor which has been developed as a part of a three-component direct-acting antiviral combination therapy. During the course of the development of the synthetic route, two novel coupling reactions were developed. First, the copper-catalyzed coupling of uracil with aryl iodides, employing picolinamide 16 as the ligand, was discovered. Later, the palladium-catalyzed sulfonamidation of aryl nonaflate 33 was developed, promoted by electron-rich palladium complexes, including the novel phosphine ligand, VincePhos (50). This made possible a convergent, highly efficient synthesis of dasabuvir that significantly reduced the mutagenic impurity burden of the process.

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“…An illustrative example is the nickel-catalyzed Kumada reaction, where naphthyl phosphate 11 – 1 reacts with an alkyl Grignard reagent ( Scheme 11 ) [ 72 ]. Additionally, the Kumada reaction catalyzed through iron and nickel complexes was used to prepare a sex pheromone of Lobesia botrana [ 73 ], (–)-piperitylmagnolol [ 74 ], and indole alkaloids [ 75 ].…”

Section: Organophosphates As Electrophiles In Transition-metal-cataly...mentioning

confidence: 99%

Organophosphates as Versatile Substrates in Organic Synthesis

Oeser,

Tobrman

2024

Molecules

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This review summarizes the applications of organophosphates in organic synthesis. After a brief introduction, it discusses cross-coupling reactions, including both transition-metal-catalyzed and transition-metal-free substitution reactions. Subsequently, oxidation and reduction reactions are described. In addition, this review highlights the applications of organophosphates in the synthesis of natural compounds, demonstrating their versatility and importance in modern synthetic chemistry.

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Synthesis of (−)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation

Cited by 8 publications

References 31 publications

N‐Iodosuccinimide (NIS) in Direct Aromatic Iodination

N‐Iodosuccinimide (NIS) in Direct Aromatic Iodination

Discovery and Development of Metal-Catalyzed Coupling Reactions in the Synthesis of Dasabuvir, an HCV-Polymerase Inhibitor

Organophosphates as Versatile Substrates in Organic Synthesis

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