Literature DB >> 16626142

Nucleophilic perfluoroalkylation of aldehydes, ketones, imines, disulfides, and diselenides.

Chaya Pooput1, William R Dolbier, Maurice Médebielle.   

Abstract

Using a procedure analogous to that developed for nucleophilic trifluoromethylation, the perfluoroalkyl anion reagents created by mixing C2F5I and n-C4F9I with tetrakis(dimethylamino)ethylene (TDAE) were effective in their nucleophilic reactions with aldehydes, ketones, imines, disulfides, and diselenides. Irradiation proved beneficial in the aldehyde and ketone reactions.

Entities:  

Year:  2006        PMID： 16626142     DOI： 10.1021/jo060250j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

1.  Copper-catalyzed trifluoromethylation of unactivated olefins.

Authors:  Andrew T Parsons; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-25       Impact factor: 15.336

2.  Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation.

Authors:  Vladimir N Boiko
Journal:  Beilstein J Org Chem       Date:  2010-08-18       Impact factor: 2.883

3.  Discovery and development of organic super-electron-donors.

Authors:  John A Murphy
Journal:  J Org Chem       Date:  2014-03-25       Impact factor: 4.354

4.  When Weaker Can Be Tougher: The Role of Oxidation State (I) in P- vs N-Ligand-Derived Ni-Catalyzed Trifluoromethylthiolation of Aryl Halides.

Authors:  Indrek Kalvet; Qianqian Guo; Graham J Tizzard; Franziska Schoenebeck
Journal:  ACS Catal       Date:  2017-01-31       Impact factor: 13.084

5.  Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines.

Authors:  Alejandra Riesco-Domínguez; Jeroen van de Wiel; Trevor A Hamlin; Bas van Beek; Stephen D Lindell; Daniel Blanco-Ania; F Matthias Bickelhaupt; Floris P J T Rutjes
Journal:  J Org Chem       Date:  2018-01-30       Impact factor: 4.354

6.  Divergent Reactivity of a Dinuclear (NHC)Nickel(I) Catalyst versus Nickel(0) Enables Chemoselective Trifluoromethylselenolation.

Authors:  Alexander B Dürr; Henry C Fisher; Indrek Kalvet; Khai-Nghi Truong; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-14       Impact factor: 15.336

7.  Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE.

Authors:  Alain Gamal Giuglio-Tonolo; Thierry Terme; Patrice Vanelle
Journal:  Molecules       Date:  2016-10-24       Impact factor: 4.411

8.  Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles.

Authors:  Cédric Spitz; Alain G Giuglio-Tonolo; Thierry Terme; Patrice Vanelle
Journal:  Molecules       Date:  2017-07-14       Impact factor: 4.411

9.  Electrophilic Trifluoromethylselenolation of Boronic Acids.

Authors:  Clément Ghiazza; Anis Tlili; Thierry Billard
Journal:  Molecules       Date:  2017-05-19       Impact factor: 4.411

10.  Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): efficient formation of products derived from aryl radicals.

Authors:  Mohan Mahesh; John A Murphy; Franck LeStrat; Hans Peter Wessel
Journal:  Beilstein J Org Chem       Date:  2009-01-12       Impact factor: 2.883
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