Literature DB >> 33414854

Amine-borane complex-initiated SF5Cl radical addition on alkenes and alkynes.

Audrey Gilbert1, Pauline Langowski1, Marine Delgado2, Laurent Chabaud2, Mathieu Pucheault2, Jean-François Paquin1.   

Abstract

The SF5Cl radical addition on unsaturated compounds was performed using an air-stable amine-borane complex as the radical initiator. This method showed to be complementary to the classic Et3B-mediated SF5Cl addition on alkenes and alkynes. A total of seven alkene and three alkyne derivatives were tested in the reaction, with yields ranging from 3% to 85%.
Copyright © 2020, Gilbert et al.; licensee Beilstein-Institut.

Entities:  

Keywords:  amine-borane complex; pentafluorosulfanyl chloride; pentafluorosulfanyl substituent; radical addition; radical initiation

Year:  2020        PMID： 33414854      PMCID： PMC7753108          DOI： 10.3762/bjoc.16.256

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN： 1860-5397            Impact factor:   2.883


  22 in total

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5.  Palladium and Raney nickel catalyzed methanolic cleavage of stable borane-amine complexes.

Authors:  M Couturier; J L Tucker; B M Andresen; P Dubé; J T Negri
Journal:  Org Lett       Date:  2001-02-08       Impact factor: 6.005

6.  Potent trifluoromethoxy, trifluoromethylsulfonyl, trifluoromethylthio and pentafluorosulfanyl containing (1,3,4-oxadiazol-2-yl)benzamides against drug-resistant Gram-positive bacteria.

Authors:  George A Naclerio; Nader S Abutaleb; Kenneth I Onyedibe; Mohamed N Seleem; Herman O Sintim
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7.  Development of Boron-Cluster-Based Progesterone Receptor Antagonists Bearing a Pentafluorosulfanyl (SF5) Group.

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Journal:  Chem Pharm Bull (Tokyo)       Date:  2019       Impact factor: 1.645

8.  Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides.

Authors:  Mélodie Birepinte; Virginie Liautard; Laurent Chabaud; Mathieu Pucheault
Journal:  Org Lett       Date:  2020-03-24       Impact factor: 6.005

9.  New and convenient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic organic compounds.

Authors:  Samia Aït-Mohand; William R Dolbier
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

10.  Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions.

Authors:  Norihito Iida; Kenta Tanaka; Etsuko Tokunaga; Satoru Mori; Norimichi Saito; Norio Shibata
Journal:  ChemistryOpen       Date:  2015-07-24       Impact factor: 2.911
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  1 in total

1.  Expanding the Repertoire of Low-Molecular-Weight Pentafluorosulfanyl-Substituted Scaffolds.

Authors:  Arathy Jose; Daniel Guest; Remi LeGay; Graham J Tizzard; Simon J Coles; Mariliza Derveni; Edward Wright; Lester Marrison; Alpha A Lee; Aaron Morris; Matt Robinson; Frank von Delft; Daren Fearon; Lizbé Koekemoer; Tetiana Matviuk; Anthony Aimon; Christopher J Schofield; Tika R Malla; Nir London; Barnaby W Greenland; Mark C Bagley; John Spencer
Journal:  ChemMedChem       Date:  2022-02-22       Impact factor: 3.540
  1 in total

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