Literature DB >> 31663758

Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF.

Raphaël Gauthier1, Marius Mamone1, Jean-François Paquin1.   

Abstract

The gold-catalyzed hydrofluorination reaction of internal alkynes using hydrofluoric acid is reported. Notably, those conditions use one of the most economical sources of HF and are free of additional additives. Both symmetrical and unsymmetrical internal alkynes can be utilized, and the use of alkynes bearing a fluorinated group at the propargylic position as substrates allowed for a regioselective hydrofluorination reaction.

Entities:  

Year:  2019        PMID: 31663758     DOI: 10.1021/acs.orglett.9b03425

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


  6 in total

1.  Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.

Authors:  Rui Guo; Xiaotian Qi; Hengye Xiang; Paul Geaneotes; Ruihan Wang; Peng Liu; Yi-Ming Wang
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-14       Impact factor: 15.336

2.  A HF Loaded Lewis-Acidic Aluminium Chlorofluoride for Hydrofluorination Reactions.

Authors:  Maëva-Charlotte Kervarec; Erhard Kemnitz; Gudrun Scholz; Svemir Rudić; Thomas Braun; Christian Jäger; Adam A L Michalchuk; Franziska Emmerling
Journal:  Chemistry       Date:  2020-05-26       Impact factor: 5.236

3.  Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes.

Authors:  Laëtitia Chausset-Boissarie; Nicolas Cheval; Christian Rolando
Journal:  Molecules       Date:  2020-11-25       Impact factor: 4.411

4.  Au(I) Catalyzed HF Transfer: Tandem Alkyne Hydrofluorination and Perfluoroarene Functionalization.

Authors:  Daniel Mulryan; Jack Rodwell; Nicholas A Phillips; Mark R Crimmin
Journal:  ACS Catal       Date:  2022-03-01       Impact factor: 13.084

5.  Gold(I) α-Trifluoromethyl Carbenes: Synthesis, Characterization and Reactivity Studies.

Authors:  Mathilde Rigoulet; David Vesseur; Karinne Miqueu; Didier Bourissou
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-03       Impact factor: 16.823

6.  Platinum-Catalyzed Hydrofluorination of Alkynes: Hydrogen Bonding to Indolylphosphine Ligands to Provide Fluoride Reactivity.

Authors:  Stefan Sander; Thomas Braun
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-26       Impact factor: 16.823

  6 in total

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