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Literature DB >> 25287968

A general palladium-catalyzed method for alkylation of heteroarenes using secondary and tertiary alkyl halides.

Xiaojin Wu¹, Jessica Wei Ting See, Kai Xu, Hajime Hirao, Julien Roger, Jean-Cyrille Hierso, Jianrong Steve Zhou.

Abstract

A general alkylation of heterocycles using a simple palladium catalyst is reported. Most classes of heterocycles, including indoles and pyridines, efficiently coupled with unactivated secondary and tertiary alkyl halides. An alkyl radical addition to neutral heteroarenes is most likely involved.

Entities: Chemical

Keywords: CH activation; alkyl radicals; heterocycles; palladium; single electron transfer

Mesh：

Substances：

Year: 2014 PMID： 25287968 DOI： 10.1002/anie.201408355

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. Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors: Alexander R O Venning; Patrick T Bohan; Erik J Alexanian
Journal: J Am Chem Soc Date: 2015-03-16 Impact factor: 15.419

2. Nickel-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors: Quentin D Tercenio; Erik J Alexanian
Journal: Tetrahedron Date: 2019-05-25 Impact factor: 2.457

3. Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles.

Authors: Crystal K Chu; Yufan Liang; Gregory C Fu
Journal: J Am Chem Soc Date: 2016-05-17 Impact factor: 15.419

A general palladium-catalyzed method for alkylation of heteroarenes using secondary and tertiary alkyl halides.

1. Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

2. Nickel-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

3. Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles.

4. Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.

5. Heterogeneous Co-catalyzed direct 2-alkylation of azoles with ethers.

6. Palladium-Catalyzed Cross Coupling of Secondary and Tertiary Alkyl Bromides with a Nitrogen Nucleophile.

7. Copper-catalyzed direct alkylation of heteroarenes.

8. The photochemical alkylation and reduction of heteroarenes.

9. Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides.

10. Selective ortho-Functionalization of Adamantylarenes Enabled by Dispersion and an Air-Stable Palladium(I) Dimer.