Literature DB >> 24259270

Controlled trifluoromethylation reactions of alkynes through visible-light photoredox catalysis.

Naeem Iqbal1, Jaehun Jung, Sehyun Park, Eun Jin Cho.   

Abstract

The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3 -containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF3 I by environmentally benign and efficient visible-light photoredox catalysis. Subtle differences in the combination of catalyst, base, and solvent enabled the control of reactivity and selectivity for the reaction between an alkyne and CF3 I.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  iridium; radical reactions; ruthenium; trifluoromethylation; visible light

Mesh:

Substances:

Year:  2013        PMID: 24259270     DOI: 10.1002/anie.201308735

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  17 in total

1.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

Review 2.  Addition of CF3 across unsaturated moieties: a powerful functionalization tool.

Authors:  Estíbaliz Merino; Cristina Nevado
Journal:  Chem Soc Rev       Date:  2014-05-02       Impact factor: 54.564

3.  Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

Authors:  Appi Reddy Mandhapati; Takayuki Kato; Takahiko Matsushita; Bashar Ksebati; Andrea Vasella; Erik C Böttger; David Crich
Journal:  J Org Chem       Date:  2015-01-20       Impact factor: 4.354

4.  Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.

Authors:  Yongquan Ning; Qinghe Ji; Peiqiu Liao; Edward A Anderson; Xihe Bi
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-07       Impact factor: 15.336

5.  Trifluoroethoxy-Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low-Energy Red-Light Irradiation.

Authors:  Kohei Matsuzaki; Tomoya Hiromura; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2017-02-21       Impact factor: 2.911

6.  Mechanisms and applications of cyclometalated Pt(ii) complexes in photoredox catalytic trifluoromethylation.

Authors:  Won Joon Choi; Sungkyu Choi; Kei Ohkubo; Shunichi Fukuzumi; Eun Jin Cho; Youngmin You
Journal:  Chem Sci       Date:  2014-11-24       Impact factor: 9.825

7.  Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions.

Authors:  Shrikant D Tambe; Kwan Hong Min; Naeem Iqbal; Eun Jin Cho
Journal:  Beilstein J Org Chem       Date:  2020-06-18       Impact factor: 2.883

8.  Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis.

Authors:  Ren Tomita; Yusuke Yasu; Takashi Koike; Munetaka Akita
Journal:  Beilstein J Org Chem       Date:  2014-05-12       Impact factor: 2.883

9.  Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex.

Authors:  Jérémy Jacquet; Sébastien Blanchard; Etienne Derat; Marine Desage-El Murr; Louis Fensterbank
Journal:  Chem Sci       Date:  2015-12-03       Impact factor: 9.825

10.  Visible-Light Photocatalytic Decarboxylation of α,β-Unsaturated Carboxylic Acids: Facile Access to Stereoselective Difluoromethylated Styrenes in Batch and Flow.

Authors:  Xiao-Jing Wei; Wout Boon; Volker Hessel; Timothy Noël
Journal:  ACS Catal       Date:  2017-09-11       Impact factor: 13.084

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