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Literature DB >> 26172446

Efficient Palladium-Catalyzed C-H Fluorination of C(sp3)-H Bonds: Synthesis of β-Fluorinated Carboxylic Acids.

Qihua Zhu¹, Dezhong Ji¹, Tingting Liang¹, Xueyan Wang¹, Yungen Xu¹.

Abstract

A novel and facile process for direct fluorination of unactivated C(sp3)-H bonds at the β position of carboxylic acids was accomplished by a palladium(II)-catalyzed C-H activation. The addition of Ag2O and pivalic acid was found to be crucial for the success of this transformation. This reaction provides a versatile strategy for the synthesis of β-fluorinated carboxylic acids.

Entities: Chemical Species

Year: 2015 PMID： 26172446 DOI： 10.1021/acs.orglett.5b01774

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

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Cited

9 in total

1. 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 2. 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

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Authors: Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal: Chem Rev Date: 2021-10-29 Impact factor: 60.622

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

5. N-Directed fluorination of unactivated Csp³-H bonds.

Authors: Emily N Pinter; Jenna E Bingham; Deyaa I AbuSalim; Silas P Cook
Journal: Chem Sci Date: 2019-12-16 Impact factor: 9.825

6. Palladium-Catalyzed Directed C(sp³)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.

Authors: Dominic P Affron; James A Bull
Journal: European J Org Chem Date: 2015-11-27

Efficient Palladium-Catalyzed C-H Fluorination of C(sp3)-H Bonds: Synthesis of β-Fluorinated Carboxylic Acids.

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

Review 2. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

5. N-Directed fluorination of unactivated Csp³-H bonds.

6. Palladium-Catalyzed Directed C(sp³)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.

7. Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids.

Review 8. Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Review 9. Bridge Functionalisation of Bicyclo[1.1.1]pentane Derivatives.

Efficient Palladium-Catalyzed C-H Fluorination of C(sp3)-H Bonds: Synthesis of β-Fluorinated Carboxylic Acids.

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

Review 2. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

5. N-Directed fluorination of unactivated Csp3-H bonds.

6. Palladium-Catalyzed Directed C(sp3)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.

7. Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids.

Review 8. Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Review 9. Bridge Functionalisation of Bicyclo[1.1.1]pentane Derivatives.

Review 2. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

5. N-Directed fluorination of unactivated Csp³-H bonds.

6. Palladium-Catalyzed Directed C(sp³)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.