Literature DB >> 20178387

Superelectrophiles and the effects of trifluoromethyl substituents.

Matthew J O'Connor1, Kenneth N Boblak, Michael J Topinka, Patrick J Kindelin, Jason M Briski, Chong Zheng, Douglas A Klumpp.   

Abstract

Trifluoromethyl-substituted superelectrophiles were generated in superacid (CF(3)SO(3)H), and their chemistry was examined. The strong electron-withdrawing properties of the trifluoromethyl group are found to enhance the electrophilic character at cationic sites in superelectrophiles. This leads to greater positive-charge delocalization in the superelectrophiles. These effects are manifested by the unusual chemo-, regio-, and stereoselectivities shown by the superelectrophiles in chemical reactions.

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Year:  2010        PMID： 20178387      PMCID： PMC2883283          DOI： 10.1021/ja1001482

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

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Authors:  Annette D. Allen; Mizue Fujio; Nageib Mohammed; Thomas T. Tidwell; Yutaka Tsuji
Journal:  J Org Chem       Date:  1997-01-24       Impact factor: 4.354

5.  BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives.

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6.  Evidence for pi-stacking as a source of stereocontrol in the synthesis of the core pyranochromene ring system common to calyxin I, calyxin J, and epicalyxin J.

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  6 in total
  6 in total

1.  Reactions of ketones with aromatics in acid media. The effect of trifluoromethyl groups and the acidity media. A theoretical study.

Authors:  Ulises Jiménez Castillo; Mikhail G Zolotukhin; Lioudmila Fomina; Daniel Romero Nieto; Lilian Olivera Garza; Serguei Fomine
Journal:  J Mol Model       Date:  2012-10-11       Impact factor: 1.810

2.  Charge delocalization and enhanced acidity in tricationic superelectrophiles.

Authors:  Rajasekhar Reddy Naredla; Chong Zheng; Sten O Nilsson Lill; Douglas A Klumpp
Journal:  J Am Chem Soc       Date:  2011-07-27       Impact factor: 15.419

3.  Mechanistic aspects of superacid mediated condensation of polyphenols with ketones. Implications for polymer synthesis.

Authors:  Gustavo López; Olivia H Cruz; Lilian I Olvera Garza; Mikhail G Zolotukhin; Serguei Fomine
Journal:  J Mol Model       Date:  2014-10-09       Impact factor: 1.810

4.  Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

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Journal:  Chem Sci       Date:  2017-03-02       Impact factor: 9.825

Review 5.  CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.

Authors:  Anthony J Fernandes; Armen Panossian; Bastien Michelet; Agnès Martin-Mingot; Frédéric R Leroux; Sébastien Thibaudeau
Journal:  Beilstein J Org Chem       Date:  2021-02-03       Impact factor: 2.883

6.  Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species.

Authors:  Dmitry S Ryabukhin; Alexey N Turdakov; Natalia S Soldatova; Mikhail O Kompanets; Alexander Yu Ivanov; Irina A Boyarskaya; Aleksander V Vasilyev
Journal:  Beilstein J Org Chem       Date:  2019-08-19       Impact factor: 2.883
  6 in total

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