Literature DB >> 29430062

Bromofluorination of Unsaturated Compounds using DMPU/HF as a Fluorinating Reagent.

Shengzong Liang1, Francis J Barrios2, Otome E Okoromoba1, Zofia Hetman1, Bo Xu3, Gerald B Hammond1.   

Abstract

Bromofluorination reactions were performed by treating of a variety of unsaturated compounds with N-bromosuccinimide (NBS) and DMPU/HF as the fluorinating reagent. The DMPU/HF complex showed to be an efficient fluorinating reagent to convert alkenes into their corresponding bromofluoro compounds. It showed to have high reactivity and the process afforded bromofluorinated products with good Markovnikov regioselectivity. These fluorinated compounds are useful starting materials and serve as building blocks for many fluorinated biologically active molecules.

Entities:  

Keywords:  Alkenes; Bromofluorination; DMPU/HF; N-bromosuccinimide; Regioselective

Year:  2017        PMID: 29430062      PMCID: PMC5804895          DOI: 10.1016/j.jfluchem.2017.07.016

Source DB:  PubMed          Journal:  J Fluor Chem        ISSN: 0022-1139            Impact factor:   2.050


  6 in total

1.  The many roles for fluorine in medicinal chemistry.

Authors:  William K Hagmann
Journal:  J Med Chem       Date:  2008-06-21       Impact factor: 7.446

2.  Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

Authors:  Otome E Okoromoba; Zhou Li; Nicole Robertson; Mark S Mashuta; Uenifer R Couto; Cláudio F Tormena; Bo Xu; Gerald B Hammond
Journal:  Chem Commun (Camb)       Date:  2016-11-08       Impact factor: 6.222

3.  Stable dialkyl ether/poly(hydrogen fluoride) complexes: dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent.

Authors:  Imre Bucsi; Béla Török; Alfonso Iza Marco; Golam Rasul; G K Surya Prakash; George A Olah
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Review 4.  Fluorine in pharmaceuticals: looking beyond intuition.

Authors:  Klaus Müller; Christoph Faeh; François Diederich
Journal:  Science       Date:  2007-09-28       Impact factor: 47.728

5.  Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.

Authors:  Otome E Okoromoba; Gerald B Hammond; Bo Xu
Journal:  Org Lett       Date:  2015-08-11       Impact factor: 6.005

6.  Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Authors:  Otome E Okoromoba; Junbin Han; Gerald B Hammond; Bo Xu
Journal:  J Am Chem Soc       Date:  2014-10-02       Impact factor: 15.419

  6 in total
  3 in total

Review 1.  Hydrogen Bonding: Regulator for Nucleophilic Fluorination.

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

2.  Solventless and Metal-free Regioselective Hydrofluorination of Functionalized Alkynes and Allenes: An Efficient Protocol for the Synthesis of gem-Difluorides.

Authors:  Zhichao Lu; Bhvandip S Bajwa; Shiwen Liu; Sheye Lee; Gerald B Hammond; Bo Xu
Journal:  Green Chem       Date:  2019-02-15       Impact factor: 10.182

3.  Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

Authors:  Shengzong Liang; Gerald B Hammond; Bo Xu
Journal:  Green Chem       Date:  2018-01-02       Impact factor: 10.182

  3 in total

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