Literature DB >> 24983328

Iodotrifluoromethylation of alkenes and alkynes with sodium trifluoromethanesulfinate and iodine pentoxide.

Zhaojia Hang1, Zejiang Li, Zhong-Quan Liu.   

Abstract

A scalable, selective, and operationally easy iodotrifluoromethylation of a wide range of alkenes and alkynes by using two simple and safe solids, sodium trifluoromethanesulfinate and iodine pentoxide, in aqueous medium has been developed. Mechanistic studies confirm that free-radical processes are involved in this system since the key radical intermediates such as CF(3) and β-CF(3) alkyl radicals have been clearly detected by spin trapping and electron spin resonance.

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Year:  2014        PMID： 24983328     DOI： 10.1021/ol501380e

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


  11 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

2.  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

3.  Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

Authors:  Hiromichi Egami; Yoshihiko Usui; Shintaro Kawamura; Sayoko Nagashima; Mikiko Sodeoka
Journal:  Chem Asian J       Date:  2015-06-16

Review 4.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

5.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

Authors:  Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

6.  Trifluoroethoxy-Coated Phthalocyanine Catalyzes Perfluoroalkylation of Alkenes under Visible-Light Irradiation.

Authors:  Kohei Matsuzaki; Tomoya Hiromora; Hideki Amii; Norio Shibata
Journal:  Molecules       Date:  2017-07-07       Impact factor: 4.411

Review 7.  Vicinal halo-trifluoromethylation of alkenes.

Authors:  Rzgar Tawfeeq Kareem; Bayan Azizi; Manzarbanou Asnaashariisfahani; Abdolghaffar Ebadi; Esmail Vessally
Journal:  RSC Adv       Date:  2021-04-21       Impact factor: 3.361

Review 8.  Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes.

Authors:  Bo Fu; Jorge Escorihuela; Jianlin Han; Santos Fustero; Pablo Barrio; Mikiko Sodeoka; Shintaro Kawamura; Alexander Sorochinsky; Vadim A Soloshonok
Journal:  Molecules       Date:  2021-11-28       Impact factor: 4.411

9.  Graphene oxide-catalyzed trifluoromethylation of alkynes with quinoxalinones and Langlois' reagent.

Authors:  Hong Li; Xiangjun Peng; Liang Nie; Lin Zhou; Ming Yang; Fan Li; Jian Hu; Zhiyang Yao; Liangxian Liu
Journal:  RSC Adv       Date:  2021-12-01       Impact factor: 3.361

10.  Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Authors:  Sadhan Jana; Ajay Verma; Rahul Kadu; Sangit Kumar
Journal:  Chem Sci       Date:  2017-07-10       Impact factor: 9.825
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