Literature DB >> 27417189

Hypervalent iodine(iii) fluorinations of alkenes and diazo compounds: new opportunities in fluorination chemistry.

Stefanie V Kohlhepp1, Tanja Gulder1.   

Abstract

The fluorination of organic molecules is a rapidly evolving and exciting field in synthesis, which still poses huge challenges despite the advances made in the past decades. Hypervalent iodine(iii) reagents, which have already proven their versatility as synthetic tools in organic chemistry, are currently on the rise in fluorination chemistry. With their ability to break new mechanistic grounds, they grant access to completely new reactivities and thus also to novel fluorinated structural scaffolds. This review aims to provide an overview of the achievements made in the iodine(iii) mediated fluorinations of aliphatic Csp2-carbon atoms with special focus on the opportunities provided by this exciting class of hypervalent substances.

Entities:  

Year:  2016        PMID: 27417189     DOI: 10.1039/c6cs00361c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  23 in total

1.  Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides.

Authors:  Moriana K Haj; Steven M Banik; Eric N Jacobsen
Journal:  Org Lett       Date:  2019-04-09       Impact factor: 6.005

Review 2.  Hydrogen Bonding: Regulator for Nucleophilic Fluorination.

Authors:  Shengzong Liang; Gerald B Hammond; Bo Xu
Journal:  Chemistry       Date:  2017-10-05       Impact factor: 5.236

3.  Oxidation of Electron-Deficient Phenols Mediated by Hypervalent Iodine(V) Reagents: Fundamental Mechanistic Features Revealed by a Density Functional Theory-Based Investigation.

Authors:  Mona Jalali; Alex C Bissember; Brian F Yates; Sarah E Wengryniuk; Alireza Ariafard
Journal:  J Org Chem       Date:  2021-08-19       Impact factor: 4.198

4.  Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes.

Authors:  Youzhi Li; Daya Huang; Ju Huang; Yan Liu; Keiji Maruoka
Journal:  J Vis Exp       Date:  2018-09-12       Impact factor: 1.355

5.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

Authors:  Biying Zhou; Moriana K Haj; Eric N Jacobsen; K N Houk; Xiao-Song Xue
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

6.  Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH2 CH2 ] → [CF2 CHF] Isosterism.

Authors:  Jessica Neufeld; Timo Stünkel; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-01       Impact factor: 15.336

Review 7.  Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes.

Authors:  Xiang Li; Pinhong Chen; Guosheng Liu
Journal:  Beilstein J Org Chem       Date:  2018-07-18       Impact factor: 2.883

8.  Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines.

Authors:  Felix Scheidt; Christian Thiehoff; Gülay Yilmaz; Stephanie Meyer; Constantin G Daniliuc; Gerald Kehr; Ryan Gilmour
Journal:  Beilstein J Org Chem       Date:  2018-05-09       Impact factor: 2.883

9.  Catalytic asymmetric nucleophilic fluorination using BF3·Et2O as fluorine source and activating reagent.

Authors:  Weiwei Zhu; Xiang Zhen; Jingyuan Wu; Yaping Cheng; Junkai An; Xingyu Ma; Jikun Liu; Yuji Qin; Hao Zhu; Jijun Xue; Xianxing Jiang
Journal:  Nat Commun       Date:  2021-06-25       Impact factor: 14.919

10.  Flow electrochemistry: a safe tool for fluorine chemistry.

Authors:  Bethan Winterson; Tim Rennigholtz; Thomas Wirth
Journal:  Chem Sci       Date:  2021-06-04       Impact factor: 9.825

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