Literature DB >> 29483850

Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds.

Xiaojun Zeng1, Zhichao Lu2, Shiwen Liu1, Gerald B Hammond2, Bo Xu1.   

Abstract

We developed an efficient synthesis of 2-fluoro-1,3-dicarbonyl compounds using readily available alkynyl ketones or esters as starting material. The key step is the insertion of hydrogen fluoride (HF) to the gold carbene intermediate generated from cationic gold catalyzed addition of N-oxides to alkynyl ketones or esters. This method gives excellent chemical yields and regioselectivity with good functional group tolerance.

Entities:  

Keywords:  1,3-Dicarbonyl Compounds; Alkynyl Esters and Ketones; Fluorination; Gold Catalysis

Year:  2017        PMID： 29483850      PMCID： PMC5824727          DOI： 10.1002/adsc.201701179

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  44 in total

1.  Ligand effects and ligand design in homogeneous gold(I) catalysis.

Authors:  Weibo Wang; Gerald B Hammond; Bo Xu
Journal:  J Am Chem Soc       Date:  2012-03-16       Impact factor: 15.419

2.  Construction of asymmetric fluorinated carbon centers.

Authors:  G K Surya Prakash; Petr Beier
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-27       Impact factor: 15.336

3.  Nucleophilic fluorination of β-ketoester derivatives with HBF4.

Authors:  Raffaele Pasceri; Hannah E Bartrum; Christopher J Hayes; Christopher J Moody
Journal:  Chem Commun (Camb)       Date:  2012-11-12       Impact factor: 6.222

4.  An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation.

Authors:  Weimin He; Chaoqun Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

5.  A practical and convenient fluorination of 1,3-dicarbonyl compounds using aqueous HF in the presence of iodosylbenzene.

Authors:  Tsugio Kitamura; Satoshi Kuriki; Mohammad Hasan Morshed; Yuji Hori
Journal:  Org Lett       Date:  2011-04-07       Impact factor: 6.005

6.  Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

Authors:  Longwu Ye; Li Cui; Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

7.  Gold-catalyzed oxidative rearrangement involving 1,2-acyl migration: efficient synthesis of functionalized dihydro-γ-carbolines from α-(2-indolyl) propargylic alcohols and imines.

Authors:  Lu Wang; Xin Xie; Yuanhong Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-03       Impact factor: 15.336

8.  Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles.

Authors:  Xiao Han; Jie Luo; Chen Liu; Yixin Lu
Journal:  Chem Commun (Camb)       Date:  2009-02-26       Impact factor: 6.222

9.  Gold-catalyzed oxidative rearrangement of homopropargylic ether via oxonium ylide.

Authors:  Mei Xu; Tian-Tian Ren; Chuan-Ying Li
Journal:  Org Lett       Date:  2012-09-06       Impact factor: 6.005

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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  2 in total

Review 1.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

2.  Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes.

Authors:  Jin-Fay Tan; Carl Thomas Bormann; Kay Severin; Nicolai Cramer
Journal:  Chem Sci       Date:  2022-02-09       Impact factor: 9.825
  2 in total

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