Literature DB >> 24571373

Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines.

Jian Cui1, Qun Jia, Ruo-Zhu Feng, Shan-Shan Liu, Tian He, Chi Zhang.   

Abstract

A widely used Lewis acid BF3·Et2O was shown to be capable of acting as an efficient fluorinating agent in an intramolecular aminofluorination reaction of homoallylic amines to provide 3-fluoropyrrolidines mediated by a commercially available hypervalent iodine(III) reagent PhIO at room temperature. A mechanism involving a carbocation intermediate was proposed on the basis of several experimental evidence.

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Year:  2014        PMID: 24571373     DOI: 10.1021/ol500238k

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Mechanism-Dependent Selectivity: Fluorocyclization of Unsaturated Carboxylic Acids or Alcohols by Hypervalent Iodine.

Authors:  Jiaqi Su; Siwei Shu; Yinwu Li; Yong Chen; Jinxiang Dong; Yan Liu; Yanxiong Fang; Zhuofeng Ke
Journal:  Front Chem       Date:  2022-05-10       Impact factor: 5.545

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

Authors:  Ying He; Zhenyu Yang; Richard T Thornbury; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-09-17       Impact factor: 15.419

3.  Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent.

Authors:  Weiming Yuan; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-09       Impact factor: 15.336

4.  Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans.

Authors:  Run Lin; Hongnan Sun; Chao Yang; Youdong Yang; Xinxin Zhao; Wujiong Xia
Journal:  Beilstein J Org Chem       Date:  2015-01-08       Impact factor: 2.883

Review 5.  Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.

Authors:  Jianlin Han; Greg Butler; Hiroki Moriwaki; Hiroyuki Konno; Vadim A Soloshonok; Tsugio Kitamura
Journal:  Molecules       Date:  2020-04-30       Impact factor: 4.411

6.  Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF3·Et2O as the Fluorine Source and Activating Reagent.

Authors:  Hongli Chai; Xiang Zhen; Xueqing Wang; Liang Qi; Yuji Qin; Jijun Xue; Zhaoqing Xu; Hongrui Zhang; Weiwei Zhu
Journal:  ACS Omega       Date:  2022-06-01

7.  Regio- and Enantioselective Intermolecular Aminofluorination of Alkenes via Iodine(I)/Iodine(III) Catalysis.

Authors:  Michael Schäfer; Timo Stünkel; Constantin G Daniliuc; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-28       Impact factor: 16.823

8.  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

  8 in total

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