Literature DB >> 28890578

Detrifluoroacetylative Generation of Halogenated Enolates: Practical Access to Perhalogenated Ketones and Alkenes.

Kaluvu Balaraman1, Max Moskowitz1, Yang Liu1, Christian Wolf1.   

Abstract

Sequential chlorination/fluorination of aromatic trifluoroacetylated ketones gives 1-aryl 2-chloro-2,4,4,4-tetrafluoro-butan-1,3-dione hydrates that are used for the synthesis of ketones and alkenes exhibiting a terminal bromochlorofluoromethyl group. The hydrates undergo detrifluoroacetylative cleavage and subsequent bromination in the presence of a copper(II)bisoxazoline catalyst, K2CO3 and NBS at room temperature. The corresponding bromochlorofluoromethyl ketones can be applied in Wittig and Horner-Wadsworth-Emmons reactions and dibromoalkenylations.

Entities:  

Year:  2016        PMID： 28890578      PMCID： PMC5589145          DOI： 10.1055/s-0035-1561433

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  8 in total

Review 1.  Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas.

Authors:  Yu Zhou; Jiang Wang; Zhanni Gu; Shuni Wang; Wei Zhu; José Luis Aceña; Vadim A Soloshonok; Kunisuke Izawa; Hong Liu
Journal:  Chem Rev       Date:  2016-01-12       Impact factor: 60.622

2.  Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions.

Authors:  Chen Xie; Lingmin Wu; Jianlin Han; Vadim A Soloshonok; Yi Pan
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-24       Impact factor: 15.336

3.  From olefination to alkylation: in-situ halogenation of Julia-Kocienski intermediates leading to formal nucleophilic iodo- and bromodifluoromethylation of carbonyl compounds.

Authors:  Yanchuan Zhao; Bing Gao; Jinbo Hu
Journal:  J Am Chem Soc       Date:  2012-03-21       Impact factor: 15.419

Review 4.  Beyond C, H, O, and N! Analysis of the elemental composition of U.S. FDA approved drug architectures.

Authors:  Brandon R Smith; Candice M Eastman; Jon T Njardarson
Journal:  J Med Chem       Date:  2014-10-06       Impact factor: 7.446

5.  Asymmetric synthesis of quaternary α-fluoro-β-keto-amines via detrifluoroacetylative Mannich reactions.

Authors:  Chen Xie; Yanling Dai; Haibo Mei; Jianlin Han; Vadim A Soloshonok; Yi Pan
Journal:  Chem Commun (Camb)       Date:  2015-06-04       Impact factor: 6.222

6.  Highly enantioselective construction of 3-hydroxy oxindoles through a decarboxylative aldol addition of trifluoromethyl α-fluorinated gem-diols to N-benzyl isatins.

Authors:  Ibrayim Saidalimu; Xiang Fang; Xiao-Peng He; Jing Liang; Xueyan Yang; Fanhong Wu
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-15       Impact factor: 15.336

7.  Amidinate salt of hexafluoroacetone hydrate for the preparation of fluorinated compounds by the release of trifluoroacetate.

Authors:  Mark V Riofski; Allison D Hart; David A Colby
Journal:  Org Lett       Date:  2012-12-14       Impact factor: 6.005

8.  Pentafluorosulfanyldifluoroacetic acid: rebirth of a promising building block.

Authors:  Andrej V Matsnev; Si-Yan Qing; Mark A Stanton; Kyle A Berger; Günter Haufe; Joseph S Thrasher
Journal:  Org Lett       Date:  2014-04-11       Impact factor: 6.005
  8 in total
  5 in total

1.  Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

Authors:  Max Moskowitz; Kaluvu Balaraman; Christian Wolf
Journal:  J Org Chem       Date:  2018-01-22       Impact factor: 4.354

2.  Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.

Authors:  Ransheng Ding; Christian Wolf
Journal:  Org Lett       Date:  2018-01-23       Impact factor: 6.005

3.  Enantioseparation and racemization of α-aryl-α-fluoroacetonitriles.

Authors:  Sarah E Steber; Angelette N D L Pham; Eryn Nelson; Christian Wolf
Journal:  Chirality       Date:  2021-10-01       Impact factor: 2.437

4.  Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2021-11-01       Impact factor: 6.005

5.  Stereoselective Synthesis of 3,3'-Bisindolines by Organocatalytic Michael Additions of Fluorooxindole Enolates to Isatylidene Malononitriles in Aqueous Solution.

Authors:  Kaluvu Balaraman; Ransheng Ding; Christian Wolf
Journal:  Adv Synth Catal       Date:  2017-09-22       Impact factor: 5.837
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.