Literature DB >> 33828616

CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.

Anthony J Fernandes1, Armen Panossian1, Bastien Michelet2, Agnès Martin-Mingot2, Frédéric R Leroux1, Sébastien Thibaudeau2.   

Abstract

"The extraordinary instability of such an "ion" accounts for many of the peculiarities of organic reactions" - Franck C. Whitmore (1932). This statement from Whitmore came in a period where carbocations began to be considered as intermediates in reactions. Ninety years later, pointing at the strong knowledge acquired from the contributions of famous organic chemists, carbocations are very well known reaction intermediates. Among them, destabilized carbocations - carbocations substituted with electron-withdrawing groups - are, however, still predestined to be transient species and sometimes considered as exotic ones. Among them, the CF3-substituted carbocations, frequently suggested to be involved in synthetic transformations but rarely considered as affordable intermediates for synthetic purposes, have long been investigated. This review highlights recent and past reports focusing on their study and potential in modern synthetic transformations.
Copyright © 2021, Fernandes et al.

Entities:  

Keywords:  carbocation; organic synthesis; superelectrophile; trifluoromethyl

Year:  2021        PMID: 33828616      PMCID: PMC7871035          DOI: 10.3762/bjoc.17.32

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


  51 in total

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Journal:  Chem Rev       Date:  2016-01-12       Impact factor: 60.622

2.  Letter: Prenyltransferase. The mechanism of the reaction.

Authors:  C D Poulter; D M Satterwhite; H C Rilling
Journal:  J Am Chem Soc       Date:  1976-05-26       Impact factor: 15.419

3.  Straightforward synthesis of novel enantiopure α-trifluoromethylated azetidine 2-carboxylic acid and homoserines.

Authors:  Nathalie Lensen; Joyce Marais; Thierry Brigaud
Journal:  Org Lett       Date:  2015-01-06       Impact factor: 6.005

4.  Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction.

Authors:  Florent Huguenot; Thierry Brigaud
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

5.  Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis.

Authors:  Gabriele Pupo; Francesco Ibba; David M H Ascough; Anna Chiara Vicini; Paolo Ricci; Kirsten E Christensen; Lukas Pfeifer; John Richard Morphy; John M Brown; Robert S Paton; Véronique Gouverneur
Journal:  Science       Date:  2018-05-11       Impact factor: 47.728

6.  Reactivity of stable trifluoroacetaldehyde hemiaminals. 2. Generation and synthetic potentialities of fluorinated iminiums.

Authors:  Thierry Billard; Bernard R Langlois
Journal:  J Org Chem       Date:  2002-02-08       Impact factor: 4.354

7.  Photochemical generation of highly destabilized vinyl cations: the effects of alpha- and beta-trifluoromethyl versus alpha- and beta-methyl substituents.

Authors:  Kaj van Alem; Geerte Belder; Gerrit Lodder; Han Zuilhof
Journal:  J Org Chem       Date:  2005-01-07       Impact factor: 4.354

8.  Selective androgen receptor modulators based on a series of 7H-[1,4]oxazino[3,2-g]quinolin-7-ones with improved in vivo activity.

Authors:  Yun Oliver Long; Robert I Higuchi; Thomas R Caferro; Thomas L S Lau; Min Wu; Marquis L Cummings; Esther A Martinborough; Keith B Marschke; William Y Chang; Francisco J López; Donald S Karanewsky; Lin Zhi
Journal:  Bioorg Med Chem Lett       Date:  2008-03-23       Impact factor: 2.823

Review 9.  Understanding organofluorine chemistry. An introduction to the C-F bond.

Authors:  David O'Hagan
Journal:  Chem Soc Rev       Date:  2007-10-17       Impact factor: 54.564

10.  Synthesis and use of a trifluoromethylated azomethine ylide precursor.

Authors:  Gaël Tran; Robin Meier; Lawrence Harris; Duncan L Browne; Steven V Ley
Journal:  J Org Chem       Date:  2012-11-30       Impact factor: 4.354

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  2 in total

1.  Formation of synthetically relevant CF3-substituted phenonium ions in superacid media.

Authors:  Anthony J Fernandes; Bastien Michelet; Armen Panossian; Agnès Martin-Mingot; Frédéric R Leroux; Sébastien Thibaudeau
Journal:  RSC Adv       Date:  2021-07-26       Impact factor: 3.361

2.  5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes.

Authors:  Ivan A Shershnev; Irina A Boyarskaya; Aleksander V Vasilyev
Journal:  Molecules       Date:  2022-10-07       Impact factor: 4.927

  2 in total

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