Light promoted metal-free regio- and stereoselective isoperfluoropropylation of unactivated alkenes with an i-C3F7-iodine(iii) reagent

文献情報

出版日 2023-11-24

DOI 10.1039/D3QO01804K

インパクトファクター 5.281

著者

Yaxing Wu, Yunchen Jiang, Fei Wang, Bin Wang, Chao Chen

原文を見る

要旨

The isoperfluoropropyl group (i-C3F7) is a large analogue of the classical CF3 group, featuring more steric hindrance and a stronger electron-withdrawing effect, and is normally considered as a “super” CF3 group and plays an irreplaceable role in pharmaceuticals and agrochemicals. Herein, a visible-light promoted metal-free regio- and stereoselective isoperfluoropropylation of various terminal alkenes and alkynes with an i-C3F7-iodine(III) (PFPI) reagent has been developed. Benefitting from the operational simplicity of the procedure and broad substrate applicability, this strategy provides a general and green way for the synthesis of various perfluoroalkylated products without the use of any metal catalysts. Detailed mechanistic experiments revealed a SET-induced concerted mechanistic pathway in the photoredox reactions and demonstrated for the first time that Ritter-type cations can undergo intramolecular elimination to generate alkenes.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Light promoted metal-free regio- and stereoselective isoperfluoropropylation of unactivated alkenes with an i-C3F7-iodine(iii) reagent

文献情報

おすすめジャーナル

関連文献

Polarization induced water molecule dissociation below the first-order electronic-phase transition temperature

Front cover

A statistical approach to inelastic electron tunneling spectroscopy on fullerene-terminated molecules

Assessment of an effective quasirelativistic methodology designed to study astatine chemistry in aqueous solution

Experimental and theoretical study of the metastable decay of negatively charged nucleosides in the gas phase

A theoretical study of pure and mixed caesium clusters and cluster ions, CslHmO 0/+n, l ≤ 5: geometry, energetics and photofragmentation

Existence of time-dependent density-functional theory for open electronic systems: Time-dependent holographic electron density theorem

Monolayer properties of uronic acid bicatenary derivatives at the air–water interface: effect of hydroxyl group stereochemistry evidenced by experimental and computational approaches

Steady-state photoinduced absorption of CdSe/CdS octapod shaped nanocrystals

The origin of dips for the graphene-based DNA sequencing device

こちらもおすすめ

6-苄基-6,7-二氢-5H-吡咯并3,4-b吡啶とは何ですか？

半硫酸奎宁单水水合物はどのように保存すればよいですか？

D-核糖-5-リン酸二ナトリウムとは何ですか？

異丙基肼はどの業界で使用されていますか？

3-乙酰基-4-羟基喹啉-2(1H)-酮はどのように合成されますか？

Bobcat339はどのように保存すればよいですか？

5-溴-4-甲基-1H-吲唑とは何ですか？

3-(4メトキシフェニル)オキテナン-3カーボイル酸の代替品はありますか？

3-イリドオキシピロロ[2,3-b]ピリジン-5-カルボキシlic酸は安全ですか？

3-氟-4- iodobenolを取り扱う際の実験室安全事項は何ですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

3-(4-Aminophenoxy)benzoic acid

1-(4-tert-Butylphenyl)ethanol

9-(1,1':4',1''-Terphenyl-4-yl)-9H-carbazole

(S)-(9H-Fluoren-9-yl)methyl (pyrrolidin-2-ylmethyl)carbamate hydrochloride

[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid

おすすめサプライヤー