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Literature DB >> 26823074

Silver-Mediated Intermolecular 1,2-Alkylarylation of Styrenes with α-Carbonyl Alkyl Bromides and Indoles.

Xuan-Hui Ouyang¹, Ren-Jie Song¹, Ming Hu¹, Yuan Yang¹, Jin-Heng Li^2,3.

Abstract

A new iron-facilitated silver-mediated radical 1,2-alkylarylation of styrenes with α-carbonyl alkyl bromides and indoles is described, and two new C-C bonds were generated in a single step through a sequence of intermolecular C(sp(3)-Br functionalization and C(sp(2))-H functionalization across the alkenes. This method provides an efficient access to alkylated indoles with broad substrate scope and excellent selectivity.

Entities: Chemical

Keywords: C−H functionalization; alkenes; heterocycles; iron; silver

Year: 2016 PMID： 26823074 DOI： 10.1002/anie.201511624

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

12 in total

1. Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

Authors: Shekhar Kc; Roshan K Dhungana; Namrata Khanal; Ramesh Giri
Journal: Angew Chem Int Ed Engl Date: 2020-03-19 Impact factor: 15.336

10. Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophiles via radical/polar crossover.

Authors: María Jesús Cabrera-Afonso; Anasheh Sookezian; Shorouk O Badir; Mirna El Khatib; Gary A Molander
Journal: Chem Sci Date: 2021-06-07 Impact factor: 9.969

Silver-Mediated Intermolecular 1,2-Alkylarylation of Styrenes with α-Carbonyl Alkyl Bromides and Indoles.

1. Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

2. Total Synthesis of (-)-Maximiscin.

3. Copper-catalyzed direct alkylation of heteroarenes.

4. Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles.

5. Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.

Review 6. Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions.

7. α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.

8. Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis.

Review 9. Iron-catalyzed domino coupling reactions of π-systems.

10. Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophiles via radical/polar crossover.