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Literature DB >> 23350845

Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides.

Shu-Yu Zhang¹, Gang He, William A Nack, Yingsheng Zhao, Qiong Li, Gong Chen.

Abstract

We report an efficient method for the alkylation of γ-C(sp(3))-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag(2)CO(3) and dibenzyl phosphate, (BnO)(2)PO(2)H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.

Entities: Chemical Species

Year: 2013 PMID： 23350845 DOI： 10.1021/ja312277g

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

37 in total

1. Ligand-Enabled Arylation of γ-C-H Bonds.

Authors: Suhua Li; Ru-Yi Zhu; Kai-Jiong Xiao; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2016-02-25 Impact factor: 15.336

2. Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Authors: Liene Grigorjeva; Olafs Daugulis
Journal: Angew Chem Int Ed Engl Date: 2014-07-24 Impact factor: 15.336

3. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides.

1. Ligand-Enabled Arylation of γ-C-H Bonds.

2. Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

3. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

5. Cobalt-promoted dimerization of aminoquinoline benzamides.

6. Pd-Catalyzed γ-C(sp³)-H Arylation of Free Amines Using a Transient Directing Group.

7. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

8. Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3.

9. Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles.

10. Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

Review 4. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.