Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Silver-catalyzed radical phosphonofluorination of unactivated alkenes.

Literature DB >> 24025164

Silver-catalyzed radical phosphonofluorination of unactivated alkenes.

Chengwei Zhang¹, Zhaodong Li, Lin Zhu, Limei Yu, Zhentao Wang, Chaozhong Li.

Abstract

We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 °C led to the efficient synthesis of β-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.

Entities: Chemical

Mesh：

Substances：

Year: 2013 PMID： 24025164 DOI： 10.1021/ja408031s

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

Keyword Cloud
Cited

12 in total

1. Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade.

Authors: J Quentin Buquoi; Jeremy M Lear; Xin Gu; David A Nagib
Journal: ACS Catal Date: 2019-05-06 Impact factor: 13.084

2. Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of α-hydroxyphosphonates induced by deoxyfluorinating reagents.

Authors: Patrycja Kaczmarek; Magdalena Rapp; Henryk Koroniak
Journal: RSC Adv Date: 2018-07-06 Impact factor: 4.036

3. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

Authors: Deng-Fu Lu; Cheng-Liang Zhu; Jeffrey D Sears; Hao Xu
Journal: J Am Chem Soc Date: 2016-08-26 Impact factor: 15.419

4. New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.

Authors: Niankai Fu; Lu Song; Jinjian Liu; Yifan Shen; Juno C Siu; Song Lin
Journal: J Am Chem Soc Date: 2019-09-09 Impact factor: 15.419

Review 5. Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors: Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal: Chem Rev Date: 2018-04-02 Impact factor: 60.622

Silver-catalyzed radical phosphonofluorination of unactivated alkenes.

1. Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade.

2. Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of α-hydroxyphosphonates induced by deoxyfluorinating reagents.

3. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

4. New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.

Review 5. Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

6. Vanadium-Catalyzed C(sp³)-H Fluorination Reactions.

7. Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.

8. A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis.

9. Hydrofluorination of Alkynes Catalysed by Gold Bifluorides.

10. A remote C-C bond cleavage-enabled skeletal reorganization: Access to medium-/large-sized cyclic alkenes.