Literature DB >> 27187724

Making the Least Reactive Electrophile the First in Class: Domino Electrophilic Activation of Amides.

Daniel Kaiser1, Nuno Maulide1.   

Abstract

The electrophilic activation of amides, especially by the action of trifluoromethanesulfonic (triflic) anhydride, enables the formation of highly electrophilic and reactive intermediates, lending themselves to diverse reaction pathways. This synopsis sets out to highlight recent advances in the field of amide activation, focused on the use of triflic anhydride, and the myriad of transformations that can ensue upon addition of several classes of electrophiles to the intermittently generated high energy intermediates.

Entities:  

Year:  2016        PMID: 27187724     DOI: 10.1021/acs.joc.6b00675

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


  26 in total

1.  Remote, Late-Stage Oxidation of Aliphatic C-H Bonds in Amide-Containing Molecules.

Authors:  Takeshi Nanjo; Emilio C de Lucca; M Christina White
Journal:  J Am Chem Soc       Date:  2017-10-04       Impact factor: 15.419

2.  Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

Authors:  Giovanni Di Mauro; Boris Maryasin; Daniel Kaiser; Saad Shaaban; Leticia González; Nuno Maulide
Journal:  Org Lett       Date:  2017-07-13       Impact factor: 6.005

3.  Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation*.

Authors:  Guoli He; Benjamin List; Mathias Christmann
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-01       Impact factor: 15.336

4.  Uniting Amide Synthesis and Activation by PIII/PV-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Authors:  Jeffrey M Lipshultz; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 16.383

5.  Mild Reductive Functionalization of Amides into N-Sulfonylformamidines.

Authors:  Paz Trillo; Tove Slagbrand; Fredrik Tinnis; Hans Adolfsson
Journal:  ChemistryOpen       Date:  2017-07-03       Impact factor: 2.911

6.  Direct Regioselective Synthesis of Tetrazolium Salts by Activation of Secondary Amides under Mild Conditions.

Authors:  Veronica Tona; Boris Maryasin; Aurélien de la Torre; Josefine Sprachmann; Leticia González; Nuno Maulide
Journal:  Org Lett       Date:  2017-05-09       Impact factor: 6.005

7.  Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates.

Authors:  Miran Lemmerer; Christopher J Teskey; Daniel Kaiser; Nuno Maulide
Journal:  Monatsh Chem       Date:  2017-11-28       Impact factor: 1.451

8.  Tertiary amine synthesis via reductive coupling of amides with Grignard reagents.

Authors:  Lan-Gui Xie; Darren J Dixon
Journal:  Chem Sci       Date:  2017-09-11       Impact factor: 9.825

9.  Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.

Authors:  Daniel Kaiser; Christopher J Teskey; Pauline Adler; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2017-11-03       Impact factor: 15.419

10.  Direct Synthesis of Enamides via Electrophilic Activation of Amides.

Authors:  Philipp Spieß; Martin Berger; Daniel Kaiser; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2021-07-07       Impact factor: 15.419

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