Literature DB >> 29334466

α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species.

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

Abstract

Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.

Entities:  

Year:  2018        PMID： 29334466     DOI： 10.1021/acs.joc.7b03058

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


  8 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.  Access to α-Pyrazole and α-Triazole Derivatives of Ketones from Oxidative Heteroarylation of Silyl Enolethers.

Authors:  Sandeep Dhanju; Aidan C Caravana; Regan J Thomson
Journal:  Org Lett       Date:  2020-10-01       Impact factor: 6.005

6.  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

7.  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 8.  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
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.