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Literature DB >> 33635665

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

Bruna S Martins¹, Daniel Kaiser¹, Adriano Bauer¹, Irmgard Tiefenbrunner¹, Nuno Maulide¹.

Abstract

A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.

Entities: Chemical Disease Species

Year: 2021 PMID： 33635665 PMCID： PMC7985840 DOI： 10.1021/acs.orglett.1c00251

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

36 in total

1. Alpha-arylation by rearrangement: on the reaction of enolates with diaryliodonium salts.

Authors: Per-Ola Norrby; Tue B Petersen; Marcin Bielawski; Berit Olofsson
Journal: Chemistry Date: 2010-07-26 Impact factor: 5.236

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

Authors: Shimon Maksymenko; Keshaba N Parida; Gulab K Pathe; Atul A More; Yuriy B Lipisa; Alex M Szpilman
Journal: Org Lett Date: 2017-11-15 Impact factor: 6.005

3. Sulfoxide-mediated α-arylation of carbonyl compounds.

Authors: Xueliang Huang; Nuno Maulide
Journal: J Am Chem Soc Date: 2011-05-16 Impact factor: 15.419

4. Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents.

Authors: Florence Malmedy; Thomas Wirth
Journal: Chemistry Date: 2016-08-19 Impact factor: 5.236

5. 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

Review 6. Metal-catalyzed alpha-arylation of carbonyl and related molecules: novel trends in C-C bond formation by C-H bond functionalization.

Authors: Carin C C Johansson; Thomas J Colacot
Journal: Angew Chem Int Ed Engl Date: 2010 Impact factor: 15.336

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

1. Alpha-arylation by rearrangement: on the reaction of enolates with diaryliodonium salts.

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

3. Sulfoxide-mediated α-arylation of carbonyl compounds.

4. Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents.

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

Review 6. Metal-catalyzed alpha-arylation of carbonyl and related molecules: novel trends in C-C bond formation by C-H bond functionalization.

7. Transition-metal-free α-arylation of β-keto amides via an interrupted insertion reaction of arynes.

8. Oxy-Allyl Cation Catalysis: An Enantioselective Electrophilic Activation Mode.

9. Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents.

10. Hypervalent Activation as a Key Step for Dehydrogenative ortho C-C Coupling of Iodoarenes.

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