Literature DB >> 27782265

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

Otome E Okoromoba1, Zhou Li1, Nicole Robertson1, Mark S Mashuta1, Uenifer R Couto2, Cláudio F Tormena2, Bo Xu3, Gerald B Hammond1.   

Abstract

We developed an efficient fluorination protocol that converts easily accessible aziridines into β-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both higher reactivity and regioselectivity and good functional group tolerance; thus, a wide scope of β-fluoroamines can now be accessed conveniently. The stereochemical behavior of the ring opening depends on the substitution pattern of the aziridine substrate.

Entities:  

Year:  2016        PMID: 27782265      PMCID: PMC5104567          DOI: 10.1039/c6cc07855a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  13 in total

1.  Phosphine-catalyzed Heine reaction.

Authors:  Allen Martin; Kathleen Casto; William Morris; Jeremy B Morgan
Journal:  Org Lett       Date:  2011-09-29       Impact factor: 6.005

2.  A novel and selective fluoride opening of aziridines by XtalFluor-E. synthesis of fluorinated diamino acid derivatives.

Authors:  Melinda Nonn; Loránd Kiss; Matti Haukka; Santos Fustero; Ferenc Fülöp
Journal:  Org Lett       Date:  2015-02-16       Impact factor: 6.005

3.  Rearrangement of beta-amino alcohols via aziridiniums: a review.

Authors:  Thomas-Xavier Métro; Béranger Duthion; Domingo Gomez Pardo; Janine Cossy
Journal:  Chem Soc Rev       Date:  2009-09-08       Impact factor: 54.564

4.  Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines.

Authors:  Julia A Kalow; Dana E Schmitt; Abigail G Doyle
Journal:  J Org Chem       Date:  2012-04-10       Impact factor: 4.354

5.  Low-temperature NMR studies of the structure and dynamics of a novel series of acid-base complexes of HF with collidine exhibiting scalar couplings across hydrogen bonds.

Authors:  Ilja G Shenderovich; Peter M Tolstoy; Nikolai S Golubev; Sergei N Smirnov; Gleb S Denisov; Hans-Heinrich Limbach
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

6.  Facile preparation of beta-fluoro amines by the reaction of aziridines with potassium fluoride dihydrate in the presence of Bu4NHSO4.

Authors:  Ren-Hua Fan; Yong-Gui Zhou; Wan-Xuan Zhang; Xue-Long Hou; Li-Xin Dai
Journal:  J Org Chem       Date:  2004-01-23       Impact factor: 4.354

7.  Highly regioselective nickel-catalyzed cross-coupling of N-tosylaziridines and alkylzinc reagents.

Authors:  Kim L Jensen; Eric A Standley; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2014-07-23       Impact factor: 15.419

8.  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
Journal:  J Am Chem Soc       Date:  2002-07-03       Impact factor: 15.419

Review 9.  Fluorine in medicinal chemistry.

Authors:  Sophie Purser; Peter R Moore; Steve Swallow; Véronique Gouverneur
Journal:  Chem Soc Rev       Date:  2007-12-13       Impact factor: 54.564

10.  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

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  12 in total

1.  Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins.

Authors:  Daniel M Sedgwick; Inés López; Raquel Román; Nanako Kobayashi; Otome E Okoromoba; Bo Xu; Gerald B Hammond; Pablo Barrio; Santos Fustero
Journal:  Org Lett       Date:  2018-04-06       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.  Bromofluorination of Unsaturated Compounds using DMPU/HF as a Fluorinating Reagent.

Authors:  Shengzong Liang; Francis J Barrios; Otome E Okoromoba; Zofia Hetman; Bo Xu; Gerald B Hammond
Journal:  J Fluor Chem       Date:  2017-08-04       Impact factor: 2.050

4.  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

5.  Multifaceted Ion Exchange Resin-Supported Hydrogen Fluoride: A Path to Flow Hydrofluorination.

Authors:  Zhichao Lu; Bhvandip S Bajwa; Otome E Okoromoba; Gerald B Hammond; Bo Xu
Journal:  Green Chem       Date:  2018-12-26       Impact factor: 10.182

6.  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

7.  HBr-DMPU: The First Aprotic Organic Solution of Hydrogen Bromide.

Authors:  Zhou Li; Rene Ebule; Jessica Kostyo; Gerald B Hammond; Bo Xu
Journal:  Chemistry       Date:  2017-08-16       Impact factor: 5.236

8.  Formation of synthetically relevant CF3-substituted phenonium ions in superacid media.

Authors:  Anthony J Fernandes; Bastien Michelet; Armen Panossian; Agnès Martin-Mingot; Frédéric R Leroux; Sébastien Thibaudeau
Journal:  RSC Adv       Date:  2021-07-26       Impact factor: 3.361

9.  Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride.

Authors:  Zhichao Lu; Xiaojun Zeng; Gerald B Hammond; Bo Xu
Journal:  J Am Chem Soc       Date:  2017-12-12       Impact factor: 15.419

10.  Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  J Org Chem       Date:  2017-12-07       Impact factor: 4.354

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