Literature DB >> 28858509

Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry.

Bibek Dhakal1, Luis Bohé2, David Crich1.   

Abstract

Although the triflate ion is not generally perceived as a nucleophile, many examples of its behavior as such exist in the literature. This Synopsis presents an overview of such reactions, in which triflate may be either a stoichiometric or catalytic nucleophile, leading to the suggestion that nucleophilic catalysis by triflate may be more common than generally accepted, albeit hidden by the typical reactivity of organic triflates which complicates their observation as intermediates.

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Year:  2017        PMID: 28858509      PMCID: PMC5600715          DOI: 10.1021/acs.joc.7b01850

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


  26 in total

1.  Why Are Vinyl Cations Sluggish Electrophiles?

Authors:  Peter A Byrne; Shinjiro Kobayashi; Ernst-Ulrich Würthwein; Johannes Ammer; Herbert Mayr
Journal:  J Am Chem Soc       Date:  2017-01-20       Impact factor: 15.419

2.  Chair interconversion and reactivity of mannuronic acid esters.

Authors:  Jerk Rönnols; Marthe T C Walvoort; Gijsbert A van der Marel; Jeroen D C Codée; Göran Widmalm
Journal:  Org Biomol Chem       Date:  2013-12-14       Impact factor: 3.876

3.  Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance.

Authors:  Tobias Gylling Frihed; Mikael Bols; Christian Marcus Pedersen
Journal:  Chem Rev       Date:  2015-04-29       Impact factor: 60.622

4.  Catalytic stereospecific O-glycosylation.

Authors:  K Kowalska; C M Pedersen
Journal:  Chem Commun (Camb)       Date:  2017-02-07       Impact factor: 6.222

5.  Synthesis of tetrahydronaphthalene lignan esters by intramolecular cyclization of ethyl p-azidophenyl-2-phenylalkanoates and evaluation of the growth inhibition of human tumor cell lines.

Authors:  Orlando Pinto; João Sardinha; Pedro D Vaz; Fátima Piedade; Maria J Calhorda; Rudolph Abramovitch; Nair Nazareth; Madalena Pinto; Maria S J Nascimento; Amélia P Rauter
Journal:  J Med Chem       Date:  2011-04-19       Impact factor: 7.446

6.  Iterative glycosylation of 2-deoxy-2-aminothioglycosides and its application to the combinatorial synthesis of linear oligoglucosamines.

Authors:  Shigeru Yamago; Takeshi Yamada; Tomokazu Maruyama; Jun-ichi Yoshida
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-13       Impact factor: 15.336

7.  Stereoselective C-glycoside formation with 2-O-benzyl-4,6-O-benzylidene protected 3-deoxy gluco- and mannopyranoside donors: comparison with O-glycoside formation.

Authors:  Myriame Moumé-Pymbock; David Crich
Journal:  J Org Chem       Date:  2012-10-11       Impact factor: 4.354

8.  Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry.

Authors:  Shinkiti Suzuki; Kouichi Matsumoto; Kohsuke Kawamura; Seiji Suga; Jun-ichi Yoshida
Journal:  Org Lett       Date:  2004-10-14       Impact factor: 6.005

9.  Cation clock permits distinction between the mechanisms of α- and β-O- and β-C-glycosylation in the mannopyranose series: evidence for the existence of a mannopyranosyl oxocarbenium ion.

Authors:  Min Huang; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2012-08-31       Impact factor: 15.419

10.  An update of the rules for pyranoside sulfonate displacement.

Authors:  Karl J Hale; Leslie Hough; Soraya Manaviazar; Andrew Calabrese
Journal:  Org Lett       Date:  2014-09-12       Impact factor: 6.005

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  6 in total

Review 1.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

2.  En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.

Authors:  David Crich
Journal:  J Am Chem Soc       Date:  2020-12-22       Impact factor: 15.419

3.  A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts.

Authors:  Łukasz Kapuśniak; Philipp N Plessow; Damian Trzybiński; Krzysztof Woźniak; Peter Hofmann; Phillip Iain Jolly
Journal:  Organometallics       Date:  2021-03-05       Impact factor: 3.876

Review 4.  Bismuth Redox Catalysis: An Emerging Main-Group Platform for Organic Synthesis.

Authors:  Hye Won Moon; Josep Cornella
Journal:  ACS Catal       Date:  2022-01-07       Impact factor: 13.084

5.  Ammonium Pertechnetate in Mixtures of Trifluoromethanesulfonic Acid and Trifluoromethanesulfonic Anhydride.

Authors:  Markus Zegke; Dennis Grödler; Maximilian Roca Jungfer; Alexander Haseloer; Meike Kreuter; Jörg M Neudörfl; Thomas Sittel; Christopher M James; Jörg Rothe; Marcus Altmaier; Axel Klein; Martin Breugst; Ulrich Abram; Erik Strub; Mathias S Wickleder
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-03       Impact factor: 16.823

6.  Reagent Controlled Stereoselective Synthesis of α-Glucans.

Authors:  Liming Wang; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

  6 in total

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