Literature DB >> 29140710

Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species.

Shimon Maksymenko1, Keshaba N Parida1, Gulab K Pathe1, Atul A More1, Yuriy B Lipisa1, Alex M Szpilman1.   

Abstract

Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles, thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic substrates is needed.

Entities:  

Year:  2017        PMID: 29140710     DOI: 10.1021/acs.orglett.7b03064

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


  10 in total

1.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

Authors:  Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal:  J Am Chem Soc       Date:  2019-12-27       Impact factor: 15.419

2.  A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species.

Authors:  Shlomy Arava; Shimon Maksymenko; Keshaba Nanda Parida; Gulab K Pathe; Atul M More; Yuriy B Lipisa; Alex M Szpilman
Journal:  J Vis Exp       Date:  2018-08-16       Impact factor: 1.355

3.  Sulfur(iv)-mediated umpolung α-heterofunctionalization of 2-oxazolines.

Authors:  Qifeng Zhang; Yuchen Liang; Ruiqi Li; Ziyi Huang; Lichun Kong; Peng Du; Bo Peng
Journal:  Chem Sci       Date:  2022-04-09       Impact factor: 9.969

4.  α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation.

Authors:  Wojciech Zawodny; Christopher J Teskey; Magdalena Mishevska; Martin Völkl; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

5.  Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones.

Authors:  Keshaba N Parida; Gulab K Pathe; Shimon Maksymenko; Alex M Szpilman
Journal:  Beilstein J Org Chem       Date:  2018-05-03       Impact factor: 2.883

6.  α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation.

Authors:  Jing Li; Adriano Bauer; Giovanni Di Mauro; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-06       Impact factor: 16.823

7.  Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.

Authors:  Quynh H Nguyen; Nguyen H Nguyen; Hanbyul Kim; Seunghoon Shin
Journal:  Chem Sci       Date:  2019-08-12       Impact factor: 9.825

8.  Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination.

Authors:  Bruna S Martins; Daniel Kaiser; Adriano Bauer; Irmgard Tiefenbrunner; Nuno Maulide
Journal:  Org Lett       Date:  2021-02-26       Impact factor: 6.005

9.  An Expedient Method for the Umpolung Coupling of Enols with Heteronucleophiles.

Authors:  Víctor García-Vázquez; Alba Carretero Cerdán; Amparo Sanz-Marco; Enrique Gómez-Bengoa; Belén Martín-Matute
Journal:  Chemistry       Date:  2022-06-17       Impact factor: 5.020

Review 10.  Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling.

Authors:  Adriano Bauer; Nuno Maulide
Journal:  Chem Sci       Date:  2021-01-07       Impact factor: 9.825

  10 in total

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