1.7 Synthesis of Difluoromethylene-Containing Compounds DOI
Yun‐Cheng Luo, Xingang Zhang

Опубликована: Янв. 1, 2024

Abstract The difluoromethylene group (CF2) is a valuable fluorinated motif that widely present in pharmaceuticals, agrochemicals, and advanced functional materials because of the unique properties fluorine atoms. Consequently, considerable efforts have been dedicated to introducing into organic molecules. This review summarizes progress synthesis difunctionalized difluoromethane (R1−CF2−FG) compounds, including methods for difluoroalkylation C—X unsaturated bonds, gem-difluorination reactions.

Язык: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Сен. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Язык: Английский

Процитировано

34

Catalytic 1,1-diazidation of alkenes DOI Creative Commons

Wangzhen Qiu,

Lihao Liao,

Xinghua Xu

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Апрель 29, 2024

Compared to well-developed catalytic 1,2-diazidation of alkenes produce vicinal diazides, the corresponding 1,1-diazidation yield geminal diazides has not been realized. Here we report an efficient approach for by redox-active selenium catalysis. Under mild conditions, electron-rich aryl with Z or E Z/E mixed configuration can undergo migratory give a series functionalized monoalkyl dialkyl that are difficult access other methods. The method is also effective construction polydiazides. formed relatively safe TGA-DSC analysis and impact sensitivity tests, be easily converted into various valuable molecules. In addition, interesting reactivity molecules via diazidomethyl moiety as formal leaving group in presence Lewis acid disclosed. Mechanistic studies revealed selenenylation-deselenenylation followed 1,2-aryl migration process involved reactions, which provides basis design new reactions.

Язык: Английский

Процитировано

2

Gem-difluorinative ring-expansion of alkenes DOI Creative Commons
Honggen Wang,

Li Yin,

Xiaobin Liu

и другие.

Опубликована: Апрель 18, 2024

Incorporating fluorine into aliphatic rings induces significant alterations in molecular conformation, acidity/basicity, and lipophilicity. Current methods for synthesizing fluorinated rings, however, involve manipulating functional groups within pre-existing ring systems. Here, we have developed a novel chemical reaction - gem-difluorinative ring-expansion of methylenecycloalkanes. The involves iodine(III) species, allows the preparation gem-difluorinated macrocyclic, fused, spiro, bridged, natural product-derived structures. protocol's practicality is demonstrated through several decagram-scale syntheses.

Язык: Английский

Процитировано

1

Straightforward Synthesis of 1‐Aryloxy‐1,1‐difluoro‐3‐aminopropan‐2‐ols – Accessing Fluorinated Derivatives of Commercialized Beta‐Blockers DOI Creative Commons
Jan-Ole Moritz, Shuang Liu,

Katharina Konieczny

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Май 24, 2024

Abstract The efficient synthesis of an array 1‐aryloxy‐1,1‐difluoro‐3‐aminopropan‐2‐ols in a one‐pot epoxidation/nucleophilic ring‐opening via the corresponding iodohydrines is described. This methodology permits construction 1,1‐difluorinated derivatives commercialized beta‐blockers addition to unprecedented members this compound class.

Язык: Английский

Процитировано

0

Hypervalent Iodine Mediated Ring-Opening 1,3-Difluorination of Benzylidenecyclopropanes DOI

Long-Ling Huang,

Jiayi Li,

Qigang Sun

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Июль 25, 2024

Abstract 1,3-Difluorinated compounds are characterized by their unique conformation, influenced 1,3-dipolar minimization effects. However, synthetic methods relatively limited. Here, a ring-opening 1,3-difluorination of benzylidenecyclopropanes (BCPs) using HF·Py, mediated an electron-poor hypervalent iodine reagent, which is generated in situ the oxidation o-nitroiodobenzene with mCPBA described. The protocol features mild reaction conditions, good functional group tolerance, and moderate to yields. Additionally, utility this method showcased further transformations olefin allylic fluoride motif.

Язык: Английский

Процитировано

0

1.7 Synthesis of Difluoromethylene-Containing Compounds DOI
Yun‐Cheng Luo, Xingang Zhang

Опубликована: Янв. 1, 2024

Abstract The difluoromethylene group (CF2) is a valuable fluorinated motif that widely present in pharmaceuticals, agrochemicals, and advanced functional materials because of the unique properties fluorine atoms. Consequently, considerable efforts have been dedicated to introducing into organic molecules. This review summarizes progress synthesis difunctionalized difluoromethane (R1−CF2−FG) compounds, including methods for difluoroalkylation C—X unsaturated bonds, gem-difluorination reactions.

Язык: Английский

Процитировано

0