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Literature DB >> 21790123

Palladium-catalyzed direct ethynylation of C(sp3)-H bonds in aliphatic carboxylic acid derivatives.

Yusuke Ano¹, Mamoru Tobisu, Naoto Chatani.

Abstract

The first catalytic alkynylation of unactivated C(sp(3))-H bonds has been accomplished. The method allows for the straightforward introduction of an ethynyl group into aliphatic acid derivatives under palladium catalysis. This new reaction can be applied to the rapid elaboration of complex aliphatic acids, for example, via azide/alkyne cycloaddition.

Entities: Chemical Species

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Year: 2011 PMID： 21790123 DOI： 10.1021/ja206002m

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

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Cited

30 in total

1. Palladium(II)-Catalyzed Site-Selective C(sp³ )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

Authors: Tao Liu; Jennifer X Qiao; Michael A Poss; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-08-07 Impact factor: 15.336

2. 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

3. Ligand-Enabled Alkynylation of C(sp³ )-H Bonds with Palladium(II) Catalysts.

Authors: Haiyan Fu; Peng-Xiang Shen; Jian He; Fanglin Zhang; Suhua Li; Peng Wang; Tao Liu; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-01-12 Impact factor: 15.336

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 direct ethynylation of C(sp3)-H bonds in aliphatic carboxylic acid derivatives.

1. Palladium(II)-Catalyzed Site-Selective C(sp³ )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

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

3. Ligand-Enabled Alkynylation of C(sp³ )-H Bonds with Palladium(II) Catalysts.

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. β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis.

6. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

7. Reversing conventional site-selectivity in C(sp³)-H bond activation.

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

9. Photoredox activation for the direct β-arylation of ketones and aldehydes.

10. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

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.